CN1760173A - Method for synthesizing o-aminophenylpropyl alcohol - Google Patents
Method for synthesizing o-aminophenylpropyl alcohol Download PDFInfo
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Abstract
A process for synthesizing O-aminophenylpropanol includes such steps as brominating reaction, addition reaction, decarboxylating reaction, carboxylating, and nitrating. Its advantage is high output rate (56-75%).
Description
Technical field
The present invention relates to a kind of synthetic method of o-aminophenylpropyl alcohol.
Background technology
All contain O at present a large amount of bioactive compoundss, heteroatomss such as N, and heterogeneous ring compound is the hugest class of number in organic compound, many materials that in physiological process, play an important role, base as nucleic acid, amino acid all includes heterocycle structure in VITAMIN and the alkaloid.People design as required some have the functional heterogeneous ring compound of special function and purposes, useful as drug, dyestuff, biosimulation material, organic conductor, engineering macromolecular material etc.So the development of heterocyclic chemistry is performed meritorious deeds never to be obliterated for the progress and the development of society.
The amino that directly is connected on the phenyl ring has certain germicidal action.The chemically reactive of o-aminophenylpropyl alcohol is also very high in addition, is a kind of intermediate of very important synthesizing heterocyclic compounds, can be by the synthetic a large amount of medicine with physiologically active of diverse ways, so its using value is very big.
Reported method is few in number at present, and wherein a kind of method is:
Though this method has only a step, raw material is that adjacent nitro styryl carbinol costs an arm and a leg, and reaction is used hydrogen and needed the special conversion unit complicated operation of autoclave.
Summary of the invention:
It is raw material with Ortho Nitro Toluene cheap and easy to get that one of purpose of the present invention is to provide a kind of, easy, the method for synthetic o-aminophenylpropyl alcohol efficiently.
For achieving the above object, the reaction mechanism that the inventive method has adopted is:
Fig. 1
According to above-mentioned reaction mechanism, the present invention adopts following technical scheme:
A kind of synthetic method of o-aminophenylpropyl alcohol is characterized in that, this method has following steps:
A. bromination reaction: with Ortho Nitro Toluene, N-bromo-succinimide and benzoyl peroxide is raw material, and tetracol phenixin is a solvent refluxing, reacts 6～8 hours; The mol ratio of Ortho Nitro Toluene, N-bromo-succinimide, benzoyl peroxide is 1: 1～1.2: 0.05; After reaction finishes, separation and purification, getting faint yellow solid is adjacent nitrobenzyl bromine;
B. addition reaction: with the tetrahydrofuran (THF) is solvent, add potassium tert.-butoxide and dimethyl malonate, under ice-water bath, stir, dripped in 0.5～5 hour with the adjacent nitrobenzyl bromine of tetrahydrofuran (THF) dissolved, the mol ratio of adjacent nitrobenzyl bromine, potassium tert.-butoxide and dimethyl malonate reaction is 1.0: 1.0～1.2: 1.0～1.2; Reacted again 1～3 hour; The alkalescence that adds saturated aqueous common salt flush away solution is quenched with ethyl acetate and to be got, and anhydrous magnesium sulfate drying filters, and spins off solvent;
C. decarboxylic reaction: in step b products therefrom, add concentrated hydrochloric acid and water.Three's mol ratio is 1: 4～7: 8～15, and heated and stirred refluxed 3～10 hours, quenches with ethyl acetate and gets, keep organic layer, spin off partial solvent, add potassium hydroxide again, make to allow the ortho-nitrophenyl propionic acid be converted into sylvite entirely, get, keep water layer with shrend, adding 10% dilute hydrochloric acid to solution pH value is 5～7, quench with ethyl acetate and to get, keep organic layer, anhydrous magnesium sulfate drying, spin off solvent, get pure ortho-nitrophenyl propionic acid;
D. reduce carboxyl: under the ice-water bath, N
2Under the gas shiled, lithium aluminium hydride added be stirred to temperature in the tetrahydrofuran solvent and drop to 0 ℃, drip with tetrahydrofuran (THF) dissolved ortho-nitrophenyl propionic acid, the dropping time was controlled at 15～50 minutes, added the back and continued reaction half an hour; The mol ratio of ortho-nitrophenyl propyl alcohol, lithium aluminium hydride is from 1.0: 4.0～4.5; Add the sodium sulfate that contains crystal water after reaction finishes and do not produce to there being bubble, add water sodium sulfate is dissolved away entirely, quench with ethyl acetate and get, keep organic layer, anhydrous magnesium sulfate drying spins off solvent and gets the ortho-nitrophenyl propyl alcohol;
E. reduce nitro: the ethanol with 50% is solvent, adds ortho-nitrophenyl propyl alcohol and iron powder and is heated to backflow, drips the concentrated hydrochloric acid of having used 10 times of alcohol dilutions again, and three's mol ratio is 1: 3: 0.12; Reacted 3～8 hours, after reaction finishes, regulator solution pH value to 7～8.5, suction filtration, the filter residue water dissolution use ethyl acetate, the reservation organic layer, anhydrous magnesium sulfate drying, filtration, be spin-dried for the product o-aminophenylpropyl alcohol.
The processing of the inventive method is very simple, removes the adjacent nitrobenzyl bromine of the first step and can purify by column chromatography when a small amount of, measure can purify through recrystallization when big outside, all the other several steps only need the acid-basicity of regulator solution.The for example purification of ortho-nitrophenyl propionic acid, because carboxylic acid becomes carboxylic acid sodium under alkaline condition water-soluble, can alkaline condition quench with organic solvent earlier down and fall not have raw material and other trace impurity of react, be transferred to acidity then with the organic solvent ortho-nitrophenyl propionic acid of quenching.The purification of o-aminophenylpropyl alcohol is also very similar, and just it is water-soluble under acidic conditions, and reason still is identical.
Reaction raw materials of the present invention is easy to get, and five step operations are simple, and equipment requirements is not high, though experience the reaction of five steps, overall yield is 56～75%, or the method for preparing o-aminophenylpropyl alcohol of less expensive.
Embodiment
Example one:
(1) in 25 milliliters of two neck round-bottomed flask that reflux condensing tube is housed, add Ortho Nitro Toluene 0.137 gram (1 mmole), N-bromo-succinimide 0.1851 gram (1.04 mmole), benzoyl peroxide 0.122 gram (0.05 mmole), 10 milliliters in tetracol phenixin, stirring heating refluxed 6 hours.After reaction finishes, use tetracol phenixin (2 * 10 milliliters) washing of heat, filtrate steams solvent with the Rotary Evaporators decompression, and (sherwood oil: ethyl acetate=10: 1) get faint yellow solid is adjacent nitrobenzyl bromine to column chromatography.
(2) 25 milliliters the bottled 5 milliliters dropping funnel of two necks, add potassium tert.-butoxide 0.1234 (1.1 mmole), 8 milliliters of tetrahydrofuran (THF)s, ice-water bath stirs down, temperature lowers the back adding with 2 milliliters of dimethyl malonates 0.1585 grams (1.2 mmole) that tetrahydrofuran (THF) is molten, stirs half an hour.Slowly dropping adds with 5 milliliters of molten adjacent nitrobenzyl bromines 0.216 grams (1 mmole) of tetrahydrofuran (THF) half an hour, reacts 2 hours again.Add the alkalescence of 15 milliliters of saturated aqueous common salt flush away solution, quench twice with 25 milliliters ethyl acetate, merge organic layer, anhydrous magnesium sulfate drying spins off solvent.
(3) product of (2) gained is joined single neck bottle of 5 milliliters, add 0.7 ml water and 1.5 milliliters of concentrated hydrochloric acid reflux 3 hours again.Quench at twice with 10 milliliters of ethyl acetate and to get, merge organic layer, spin off partial solvent, remain about 5 milliliters.Hydro-oxidation potassium 0.112 gram (2 mmole) in organic layer, allow the ortho-nitrophenyl propionic acid be converted into sodium salt entirely, quench at twice with 10 ml waters and to get, combining water layer adds 10% dilute hydrochloric acid to subacidity, quenches at twice with 20 milliliters of ethyl acetate and gets, merge organic layer, anhydrous magnesium sulfate drying spins off solvent, gets pure ortho-nitrophenyl propionic acid.
(4) 25 milliliters the bottled 5 milliliters constant pressure funnel of two necks is air N
2Gas is replaced, N
2Add lithium aluminium hydride 0.1518 gram (4 mmole) under the gas shiled, 10 milliliters of tetrahydrofuran (THF) ice-water baths stirred 20 minutes down.Ortho-nitrophenyl propionic acid 0.193 gram (1 mmole) that is dissolved in 5 milliliters of tetrahydrofuran (THF)s with syringe holder is injected into constant pressure funnel, drips in 5 minutes, continues reaction 15 minutes.Add the sodium sulfate that contains crystal water after reaction finishes and do not produce to there being bubble, add water sodium sulfate is dissolved away entirely, quench at twice with 25 milliliters of ethyl acetate and get, merge organic layer, anhydrous magnesium sulfate drying spins off solvent and gets the ortho-nitrophenyl propyl alcohol.
(5) in 25 milliliters of two neck round-bottomed flasks that reflux condensing tube is housed, add ortho-nitrophenyl propyl alcohol 0.179 gram (1 mmole), iron powder 0.168 gram (3 mmole), 10 milliliter of 50% ethanol is heated to backflow.After the backflow, the concentrated hydrochloric acid of 0.0017 milliliter (0.12 mmole) is added drop-wise in the reaction flask for 10 times with 50% alcohol dilution, continues reaction three and a half hours.Add the ethanol that contains 15% potassium hydroxide to alkalescence, suction filtration, filtrate spins off ethanol, adds 5 ml waters, quench with 10 milliliters of ethyl acetate and get twice, the merging organic layer, anhydrous magnesium sulfate drying, be spin-dried for o-aminophenylpropyl alcohol.
Example two:
(1) in 50 milliliters of two neck round-bottomed flask that reflux condensing tube is housed, add Ortho Nitro Toluene 1.37 grams (10 mmole), N-bromo-succinimide 1.851 grams (10.4 mmole), benzoyl peroxide 1.22 grams (0.5 mmole), 25 milliliters in tetracol phenixin, stirring heating refluxed 6 hours.After reaction finishes, use tetracol phenixin (2 * 20 milliliters) washing of heat, filtrate steams solvent with the Rotary Evaporators decompression, and (sherwood oil: ethyl acetate=10: 1) get faint yellow solid is adjacent nitrobenzyl bromine to column chromatography.
(2) 50 milliliters the bottled 10 milliliters dropping funnel of two necks, add potassium tert.-butoxide 1.234 (11 mmole), 25 milliliters of tetrahydrofuran (THF)s, ice-water bath stirs down, temperature lowers the back adding with 3 milliliters of dimethyl malonates 1.585 grams (12 mmole) that tetrahydrofuran (THF) is molten, stirs half an hour.Slowly dropping added with 8 milliliters of molten adjacent nitrobenzyl bromines 2.16 grams (10 mmole) of tetrahydrofuran (THF) in 2 hours, reacted 2 hours again.Add the alkalescence of 25 milliliters of saturated aqueous common salt flush away solution, quench twice with 30 milliliters ethyl acetate, merge organic layer, anhydrous magnesium sulfate drying spins off solvent.
(3) product of (2) gained is joined single neck bottle of 50 milliliters, add 7 ml waters and 15 milliliters of concentrated hydrochloric acid reflux 5 hours again.Quench at twice with 25 milliliters of ethyl acetate and to get, merge organic layer, spin off partial solvent.Hydro-oxidation potassium 1.12 grams (20 mmole) in organic layer, allow the ortho-nitrophenyl propionic acid be converted into sodium salt entirely, quench at twice with 25 ml waters and to get, combining water layer adds 10% dilute hydrochloric acid to subacidity, quenches at twice with 40 milliliters of ethyl acetate and gets, merge organic layer, anhydrous magnesium sulfate drying spins off solvent, gets pure ortho-nitrophenyl propionic acid.
(4) 50 milliliters the bottled 10 milliliters constant pressure funnel of two necks is air N
2Gas is replaced, N
2Add lithium aluminium hydride 1.518 grams (40 mmole) under the gas shiled, be stirred to 0 ℃ under 25 milliliters of tetrahydrofuran (THF) ice-water baths.Ortho-nitrophenyl propionic acid 1.93 grams (10 mmole) that are dissolved in 8 milliliters of tetrahydrofuran (THF)s with syringe holder are injected into constant pressure funnel, drip in 15 minutes, continue to react half an hour.Add the sodium sulfate that contains crystal water and do not produce to there being bubble, add water sodium sulfate is dissolved away entirely, quench at twice with 30 milliliters of ethyl acetate and get, merge organic layer, anhydrous magnesium sulfate drying spins off solvent and gets the ortho-nitrophenyl propyl alcohol.
(5) in 50 milliliters of two neck round-bottomed flasks that reflux condensing tube is housed, add ortho-nitrophenyl propyl alcohol 1.79 grams (10 mmole), iron powder 1.68 grams (30 mmole), 25 milliliter of 50% ethanol is heated to backflow.After the backflow, the concentrated hydrochloric acid of 0.017 milliliter (1.2 mmole) is added drop-wise in the reaction flask for 10 times with 50% alcohol dilution, continues reaction three and a half hours.Add the ethanol that contains 15% potassium hydroxide to alkalescence, suction filtration, filtrate spins off ethanol, adds 20 ml waters, quench with 40 milliliters of ethyl acetate and get twice, the merging organic layer, anhydrous magnesium sulfate drying, be spin-dried for o-aminophenylpropyl alcohol.
Example three:
(1) in 1 liter of two neck round-bottomed flask that reflux condensing tube is housed, add Ortho Nitro Toluene 137 grams (1 mole), N-bromo-succinimide 185.1 grams (1.04 moles), benzoyl peroxide 122 grams (0.05 mole), 600 milliliters in tetracol phenixin, stirring heating refluxed 7 hours.After reaction finished, with tetracol phenixin (2 * 200 milliliters) washing of heat, filtrate steamed solvent with the Rotary Evaporators decompression, and (sherwood oil: ethyl acetate=10: 1) to get faint yellow solid be adjacent nitrobenzyl bromine to recrystallization to solubilizing agent.
(2) 1 liters the bottled 200 milliliters dropping funnel of two necks, add potassium tert.-butoxide 123.4 (1.1 moles), 500 milliliters of tetrahydrofuran (THF)s, ice-water bath stirs down, temperature lowers the back adding with 50 milliliters of dimethyl malonates 158.5 grams (1.2 moles) that tetrahydrofuran (THF) is molten, stirs 1 hour.Slowly dropping added with 100 milliliters of molten adjacent nitrobenzyl bromines 216 grams (1 mole) of tetrahydrofuran (THF) in 4 hours, reacted four and a half hours again.Add the alkalescence of 300 milliliters of saturated aqueous common salt flush away solution, quench twice with 500 milliliters ethyl acetate, merge organic layer, anhydrous magnesium sulfate drying spins off solvent.
(3) product of (2) gained is joined 2 liters two neck bottles, add 330 ml waters and 750 milliliters of concentrated hydrochloric acid reflux 8 hours again.Quench at twice with 1.5 liters of ethyl acetate and to get, merge organic layer, spin off partial solvent.Hydro-oxidation potassium 112 grams (2 moles) in organic layer, allow the ortho-nitrophenyl propionic acid be converted into sodium salt entirely, quench at twice with 1 premium on currency and to get, combining water layer adds 10% dilute hydrochloric acid to subacidity, quenches at twice with 1.5 liters of ethyl acetate and gets, merge organic layer, anhydrous magnesium sulfate drying spins off solvent, gets pure ortho-nitrophenyl propionic acid.
(4) 1 liters the bottled 200 milliliters constant pressure funnel of two necks is air N
2Gas is replaced, N
2Add lithium aluminium hydride 151.8 grams (4 moles) under the gas shiled, be stirred to 0 ℃ under 500 milliliters of tetrahydrofuran (THF) ice-water baths.Ortho-nitrophenyl propionic acid 193 grams (1 mole) that are dissolved in 150 milliliters of tetrahydrofuran (THF)s with syringe holder are injected into constant pressure funnel, drip in 45 minutes, continue to react half an hour.Add the sodium sulfate that contains crystal water and do not produce to there being bubble, add water sodium sulfate is dissolved away entirely, quench at twice with 800 milliliters of ethyl acetate and get, merge organic layer, anhydrous magnesium sulfate drying spins off solvent and gets the ortho-nitrophenyl propyl alcohol.
(5) in 1 liter of two neck round-bottomed flask that reflux condensing tube is housed, add ortho-nitrophenyl propyl alcohol 179 grams (1 mole), iron powder 168 grams (3 moles), 500 milliliter of 50% ethanol is heated to backflow.After the backflow, the concentrated hydrochloric acid of 1.7 milliliters (0.12 moles) is added drop-wise in the reaction flask for 10 times with 50% alcohol dilution, continues reaction five and a half hours.Add the ethanol that contains 15% potassium hydroxide to alkalescence, suction filtration, filtrate spins off ethanol, adds 500 ml waters, quench with 1 liter of ethyl acetate and get twice, the merging organic layer, anhydrous magnesium sulfate drying, be spin-dried for o-aminophenylpropyl alcohol.
Example four:
(1) in 2 liters of two neck round-bottomed flask that reflux condensing tube is housed, add Ortho Nitro Toluene 342.5 grams (2.5 moles), N-bromo-succinimide 462.8 grams (2.6 moles), benzoyl peroxide 305 grams (0.75 mole), 1200 milliliters in tetracol phenixin, stirring heating refluxed 8 hours.After reaction finished, with tetracol phenixin (2 * 250 milliliters) washing of heat, filtrate steamed solvent with the Rotary Evaporators decompression, and (sherwood oil: ethyl acetate=10: 1) to get faint yellow solid be adjacent nitrobenzyl bromine to recrystallization to solubilizing agent.
(2) 2 liters the bottled 500 milliliters dropping funnel of two necks, add potassium tert.-butoxide 308.5 (2.75 moles), 1000 milliliters of tetrahydrofuran (THF)s, ice-water bath stirs down, temperature lowers the back adding with 100 milliliters of dimethyl malonates 396.2 grams (3 moles) that tetrahydrofuran (THF) is molten, stirs 1.5 hours.Slowly dropping added with 200 milliliters of molten adjacent nitrobenzyl bromines 540 grams (2.5 moles) of tetrahydrofuran (THF) in 5 hours, reacted five hours again.Add the alkalescence of 600 milliliters of saturated aqueous common salt flush away solution, quench twice with 1000 milliliters ethyl acetate, merge organic layer, anhydrous magnesium sulfate drying spins off solvent.
(3) product of (2) gained is joined 4 liters two neck bottles, add 710 ml waters and 1430 milliliters of concentrated hydrochloric acid reflux 8 hours again.Quench at twice with 3 liters of ethyl acetate and to get, merge organic layer, spin off partial solvent.Hydro-oxidation potassium 280 grams (5 moles) in organic layer, allow the ortho-nitrophenyl propionic acid be converted into sodium salt entirely, quench at twice with 2 premium on currency and to get, combining water layer adds 10% dilute hydrochloric acid to subacidity, quenches at twice with 3 liters of ethyl acetate and gets, merge organic layer, anhydrous magnesium sulfate drying spins off solvent, gets pure ortho-nitrophenyl propionic acid.
(4) 2 liters the bottled 500 milliliters constant pressure funnel of two necks is air N
2Gas is replaced, N
2Add lithium aluminium hydride 379.5 grams (10 moles) under the gas shiled, be stirred to 0 ℃ under 1000 milliliters of tetrahydrofuran (THF) ice-water baths.Ortho-nitrophenyl propionic acid 482.5 grams (2.5 moles) that are dissolved in 300 milliliters of tetrahydrofuran (THF)s with syringe holder are injected into constant pressure funnel, drip in 50 minutes, continue to react half an hour.Add the sodium sulfate that contains crystal water and do not produce to there being bubble, add water sodium sulfate is dissolved away entirely, quench at twice with 1500 milliliters of ethyl acetate and get, merge organic layer, anhydrous magnesium sulfate drying spins off solvent and gets the ortho-nitrophenyl propyl alcohol.
(5) in 2 liters of two neck round-bottomed flasks that reflux condensing tube is housed, add ortho-nitrophenyl propyl alcohol 447.5 grams (2.5 moles), iron powder 420 grams (7.5 moles), 1000 milliliter of 50% ethanol is heated to backflow.After the backflow, the concentrated hydrochloric acid of 4.25 milliliters (0.3 moles) is added drop-wise in the reaction flask for 10 times with 50% alcohol dilution, continues reaction six and a half hours.Add the ethanol that contains 15% potassium hydroxide to alkalescence, suction filtration, filtrate spins off ethanol, adds 1000 ml waters, quench with 2 liters of ethyl acetate and get twice, the merging organic layer, anhydrous magnesium sulfate drying, be spin-dried for o-aminophenylpropyl alcohol.
Claims (1)
1. the synthetic method of an o-aminophenylpropyl alcohol is characterized in that, this method has following steps:
A. bromination reaction: with Ortho Nitro Toluene, N-bromo-succinimide and benzoyl peroxide is raw material, and tetracol phenixin is a solvent refluxing, reacts 6～8 hours; The mol ratio of Ortho Nitro Toluene, N-bromo-succinimide, benzoyl peroxide is 1: 1～1.2: 0.05; After reaction finishes, through column chromatography or recrystallization, separation and purification, getting faint yellow solid is adjacent nitrobenzyl bromine;
B. addition reaction: with the tetrahydrofuran (THF) is solvent, add potassium tert.-butoxide and dimethyl malonate, under ice-water bath, stir, dripped in 0.5～5 hour with the adjacent nitrobenzyl bromine of tetrahydrofuran (THF) dissolved, the mol ratio of adjacent nitrobenzyl bromine, potassium tert.-butoxide and dimethyl malonate reaction is 1.0: 1.0～1.2: 1.0～1.2; Reacted again 1～3 hour; The alkalescence that adds saturated aqueous common salt flush away solution is quenched with ethyl acetate and to be got, and anhydrous magnesium sulfate drying filters, and spins off solvent;
C. decarboxylic reaction: in step b products therefrom, add concentrated hydrochloric acid and water.Three's mol ratio is 1: 4～7: 8～15, and heated and stirred refluxed 3～10 hours, quenches with ethyl acetate and gets, keep organic layer, spin off partial solvent, add potassium hydroxide again, make to allow the ortho-nitrophenyl propionic acid be converted into sylvite entirely, get, keep water layer with shrend, adding 10% dilute hydrochloric acid to solution pH value is 5～7, quench with ethyl acetate and to get, keep organic layer, anhydrous magnesium sulfate drying, spin off solvent, get pure ortho-nitrophenyl propionic acid;
D. reduce carboxyl: under the ice-water bath, N
2Under the gas shiled, lithium aluminium hydride added be stirred to temperature in the tetrahydrofuran solvent and drop to 0 ℃, drip with tetrahydrofuran (THF) dissolved ortho-nitrophenyl propionic acid, the dropping time was controlled at 15～50 minutes, added the back and continued reaction half an hour; The mol ratio of ortho-nitrophenyl propyl alcohol, lithium aluminium hydride is from 1.0: 4.0～4.5; Add the sodium sulfate that contains crystal water after reaction finishes and do not produce to there being bubble, add water sodium sulfate is dissolved away entirely, quench with ethyl acetate and get, keep organic layer, anhydrous magnesium sulfate drying spins off solvent and gets the ortho-nitrophenyl propyl alcohol;
E. reduce nitro: the ethanol with 50% is solvent, adds ortho-nitrophenyl propyl alcohol and iron powder and is heated to backflow, drips the concentrated hydrochloric acid of having used 10 times of alcohol dilutions again, and three's mol ratio is 1: 3: 0.12; Reacted 3～8 hours, after reaction finishes, regulator solution pH value to 7～8.5, suction filtration, the filter residue water dissolution use ethyl acetate, the reservation organic layer, anhydrous magnesium sulfate drying, filtration, be spin-dried for the product o-aminophenylpropyl alcohol.
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Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102584548A (en) * | 2011-01-11 | 2012-07-18 | 中美华世通生物医药科技（武汉）有限公司 | Preparation method for bromine benzyls compound |
| CN106977404A (en) * | 2017-04-17 | 2017-07-25 | 安徽广信农化股份有限公司 | A kind of integral type synthesis system of pyraclostrobin intermediate adjacent nitro benzyl bromine |
| CN107098812A (en) * | 2017-04-17 | 2017-08-29 | 安徽广信农化股份有限公司 | A kind of synthesis technique of pyraclostrobin intermediate adjacent nitro benzyl bromine |
| CN108033888A (en) * | 2017-10-27 | 2018-05-15 | 苏州盖德精细材料有限公司 | A kind of preparation method of equal amido phenenyl alcohol |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5962737A (en) * | 1997-01-08 | 1999-10-05 | West; Daniel David | 2-amino-1-phenylpropanols, stereospecific synthesis thereof, and method of optically resolving the same |
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2005
- 2005-10-27 CN CNB2005100307415A patent/CN100357256C/en not_active Expired - Fee Related
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102584548A (en) * | 2011-01-11 | 2012-07-18 | 中美华世通生物医药科技（武汉）有限公司 | Preparation method for bromine benzyls compound |
| CN102584548B (en) * | 2011-01-11 | 2014-03-26 | 中美华世通生物医药科技（武汉）有限公司 | Preparation method for bromine benzyls compound |
| CN106977404A (en) * | 2017-04-17 | 2017-07-25 | 安徽广信农化股份有限公司 | A kind of integral type synthesis system of pyraclostrobin intermediate adjacent nitro benzyl bromine |
| CN107098812A (en) * | 2017-04-17 | 2017-08-29 | 安徽广信农化股份有限公司 | A kind of synthesis technique of pyraclostrobin intermediate adjacent nitro benzyl bromine |
| CN108033888A (en) * | 2017-10-27 | 2018-05-15 | 苏州盖德精细材料有限公司 | A kind of preparation method of equal amido phenenyl alcohol |
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