Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
  • C07C41/01—Preparation of ethers
  • C07C41/16—Preparation of ethers by reaction of esters of mineral or organic acids with hydroxy or O-metal groups
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C43/00—Ethers; Compounds having groups, groups or groups
  • C07C43/02—Ethers
  • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
  • C07C43/04—Saturated ethers
  • C07C43/12—Saturated ethers containing halogen
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C43/00—Ethers; Compounds having groups, groups or groups
  • C07C43/02—Ethers
  • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
  • C07C43/04—Saturated ethers
  • C07C43/12—Saturated ethers containing halogen
  • C07C43/126—Saturated ethers containing halogen having more than one ether bond
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C43/00—Ethers; Compounds having groups, groups or groups
  • C07C43/02—Ethers
  • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
  • C07C43/04—Saturated ethers
  • C07C43/13—Saturated ethers containing hydroxy or O-metal groups
  • C07C43/137—Saturated ethers containing hydroxy or O-metal groups containing halogen
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C43/00—Ethers; Compounds having groups, groups or groups
  • C07C43/02—Ethers
  • C07C43/03—Ethers having all ether-oxygen atoms bound to acyclic carbon atoms
  • C07C43/14—Unsaturated ethers
  • C07C43/17—Unsaturated ethers containing halogen
• • C—CHEMISTRY; METALLURGY
  • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
  • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
  • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
  • C09K23/007—Organic compounds containing halogen

Definitions

• Phenyltrichlormethylethers synthesized with SbF 3 in the presence of SbCl 5 The common method for introducing CF 3 O groups into aromatic rings was developed in 1964 by WA Sheppard. This method is based on fluorination by means of sulfur tetrafluoride of aryl fluoroformates formed by reaction of phenols with difluorophosgene (WA Sheppard, J. Org. Chem., Vol. 29, 1964, No. 1, pp. 1-11).
• DBH 1,3-dibromo-5,5-dimethylhydantione
• WO 2006/072401 describes compounds which carry at least one terminal trifluoromethoxy group and have a polar end group, are surface-active and are outstandingly suitable as surfactants.
• a first subject of the present invention is a process for the preparation of at least one CF 3 O group-containing compounds comprising at least the reaction of CF 3 O " salts with compounds of the formula (I)
• Y -HaI, -OSO 2 (CF 2 ) Z F, -OSO 2 C 2 H 22 + 1 , -OSO 2 F, -OSO 2 Cl, -OC (O) CF 3 , or -OSO 2 Ar,
• L independently of one another a single bond or a linear or branched (CR 3 R 4 ) q- alkyl, optionally containing at least one aromatic ring, cycloalkyl, heterocyclic ring, O atom, S atom,
• R aryl or cycloalkyl or alkylaryl (eg benzyl), optionally with at least one fluorine and / or chlorine and / or bromine and / or iodine atom and / or other functional group (such as NO 2 , NH 2 , CN , C (O) R, C (O) OR, C (O) NR 2 ), linear or branched H (CR 3 R 4 ) r -alkyl
• R 1 to 20
• R 1 , R 2 , R 3 and R 4 independently H, aryl, cycloalkyl, optionally substituted by at least one fluorine and / or chlorine atom, linear or branched alkyl, optionally containing at least one aromatic ring, heterocyclic ring, O atom, S - Atom, double bond and / or triple bond and optionally substituted with at least one fluorine and / or chlorine atom
• CH n and L 0 may together form a cycloalkyl or aromatic ring or heterocyclic ring.
• R 1 and R 2 are preferably independently of one another H or methyl.
• R 3 and R 4 are preferably independently of one another H or linear or branched C 1 -C 6 -alkyl or cycloalkyl.
• a preferred embodiment of the method according to the invention consists in the use of compounds which have combinations of the above-mentioned. contain preferred variables, in particular those in which all preferred forms of the variables occur.
• L linear or branched (CR 3 R 4 ) q- alkyl, optionally containing at least one O atom,
• R 1 and R 2 independently of one another H or methyl
• R 3 and R 4 independently of one another H and / or linear or branched
• C 1 - C 6 is alkyl or cycloalkyl.
• the compounds of the formula (I) to be used according to the invention may contain the groups Y once, twice or three times, preferably simply.
• the groups Y can also be included several times.
• For the reaction of the compounds of the formula (I) can be used all known CF 3 O "salts.
• Ths (dimethylamino) sulfonium cation (as guanidinium salt).
• (R 5 ) 4 N + CF 3 O ⁇ salts, wherein R 5 independently of one another may be C 1 -C 4 -alkyl, in particular C 1 -C 2 -alkyl, are used.
• Another object of the present invention is a process for the preparation of at least one CF 3 O group-containing compounds comprising the use of KOCF 3 and / or RbOCF 3 .
• KOCF 3 and RbOCF 3 can be formed in situ.
• RbOCF 3 can also be added separately. Particularly preferred is the use of RbOCF 3 .
• RbOCF 3 formed in situ or as a substance in the reaction of allyl bromide or iodide, in particular allyl iodide, compared to Cs + CF 3 O " salts better results (the proportion of byproduct allyl fluoride is low ) and requires no expensive autoclave technology.
• the reactions of the compounds of the formula (I) with the CF 3 O " salts are preferably carried out at temperatures from -30 to 120 ° C., particularly preferably from 0 ° C. to 100 ° C., very particularly preferably from room temperature to 80 0 C.
• temperatures between 0 C and 8O 0 C is required.
• the preferred temperature is particularly reactive X groups (for example, -OSO 2 CF 3) between O 0 C and 30 0 C.
• the temperature is between 30 and 80 ° C.
• reaction times depend on the reactivity of the reactants used. They are depending on the case between 1 hour and up to 36 hours.
• the processes of the invention can be carried out at atmospheric pressure.
• a reaction under elevated pressure eg. B. in the autoclave, is not necessary.
• Preferred solvents for the reactions with CF 3 O ⁇ salts are organic solvents, particularly preferably polar aprotic solvents.
• the reaction can be carried out in acetonitrile, N 1 N-
• Dimethylformamide, N, N-dimethylacetamide, N-methylpyrrolidone and / or other amides of secondary amines Particularly preferred are N 1 N- dimethylformamide, N, N-dimethylacetamide and / or N-methylpyrrolidone.
• Another object of the present invention is also a preparation process for KOCF 3 and RbOCF 3 after which KF or RbF is reacted with trifluoromethyl triflate or Difluorphosgen, as exemplified in the following scheme for RbOCF 3 .
• the production by means of trifluoromethyl triflate is particularly preferred.
• the reaction is preferably carried out at temperatures from -60 0 C to 30 0 C, more preferably from -30 ° C to room temperature, most preferably at -20 ° C to 0 ° C.
• Preferred solvents for the production of KOCF 3 and RbOCF 3 are organic solvents, more preferably polar aprotic solvents.
• the reaction can be carried out in acetonitrile, N 1 N-
• N 1 N- dimethylformamide NN-dimethylacetamide and / or N-methylpyrrolidone.
• Another object of the present invention are compounds of the formula (II)
• Preferred compounds of the formula (II) are also those in which X is H.
• the compounds of the formula (II) according to the invention containing the OCF 3 group one, two or three times, preferably simply.
• the OCF 3 group can also be included several times.
• Examples of such structures are the following compounds 3-trifluoromethoxy-2-trifluoromethoxymethyl-propene (A), 1, 3-bis-trifluoromethoxy-propan-2-one (B), 6-trifluoromethoxy-5-trifluoromethoxymethyl-hex-1-ene (C) and (2-benzyloxymethyl-6-trifluoromethoxy-hexyloxymethyl) -benzene (D).
• the compounds of the formula (I) according to the invention can be prepared by processes known to the person skilled in the art. In particular, the reaction of alcohols of the formula (III))
• the byproduct pyridinium triflate is preferably removed after the first reaction step.
• the HCl formed is removed, e.g. Example by adding a base such as pyridine or triethylamine or by complexing with dioxane and distillative removal of the complex formed
• This reaction can also be carried out in the presence of KF, which not only replaces Cl with F but also captures as the base HF.
• CH 2 CH (CH 2) n OH + CISO 2 CI + C 4 H 8 O 2 - *
• CH 2 CH (CH 2) n OSO 2 Cl + C 4 H 8 O 2 -HCI
• the compounds of the formula (II) according to the invention can be used in various synthesis processes for the preparation of organic compounds containing CF 3 O groups. They are z. As suitable for hydrolysis, nucleophilic substitution, oxidation, epoxidation, hydrogenation, hydroboration with the following oxidation, metathesis of olefins, and other reactions known in the art.
• the compounds according to the invention can be used in particular for the preparation of compounds of the general formulas (IV), (V) and (VI), where L and X have the meanings described above and X can in particular also be an OH group.
• the compounds of formula (II) can be used to prepare CF 3 O group-containing surface active compound.
• Such compounds are used as interfacial or emulsifier, particularly in the manufacture and use of fluoropolymers. Further applications of the compounds according to the invention are described in WO 2006/072401.
• a particular advantage of the present invention may in particular be that no autoclave technique is necessary, that the yields can be improved and that inexpensive and commercially available educts can be used.
• Another advantage is the use of many starting materials, especially those of the formula (I), since the present method is not limited only to allyl compounds. It is of particular advantage that the rubidium salt can be regenerated.
• Example 2b allyl trifluoromethyl ether CF 3 SO 2 OCF 3 + KF '5 ° C D b ⁇ S A 0 ° C > KOCF 3 + CF 3 SO 2 F,
• DMA Dimethylacetamide
• reaction mixture by means of a cooled to -40 0 C bath added.
• the reaction mixture is maintained at 30 -20 0 C, 1 hour at O 0 C and 30 min at 20 ° C min. Thereafter, the temperature of the reflux condenser is at - 20 0 C increased to remove the Trifluormethylsulfonylfluorid, CF 3 SO 2 F, which is formed in the reaction.
• Acetonitrile is decanted, the
• Trifluoromethyl triflate CF 3 SO 2 OCF 3 added.
• 0.25 g (2.9 mmol) of N, N-dimethylacetamide (DMA) are slowly added by means of a bath cooled to 0 ° C.
• the reaction mixture is kept at 0 ° C. for three hours. Thereafter, the temperature of the reflux condenser is raised to room temperature to remove the trifluoromethylsulfonyl fluoride, CF 3 SO 2 F, which is formed in the reaction.
• the DMA is removed at 0 ° C. under reduced pressure and the white product is dried at 0 ° C. under reduced pressure (10 -3 mbar). There are obtained 5.0 g of a white solid.
• the yield of potassium trifluoromethoxylate is 55% based on KF.
• the product, KOCF 3 is characterized by Raman spectroscopy. (Melting point tube, 892 mW). 1544 cm “1 vi Ai CO stretching vibration
• Reaction mixture added by means of a -45 ° C cooled bath.
• the reaction mixture is held for 2.5 hours at -25 ° C, for 1 hour at 0 0 C and for 1 hour at 2O 0 C. Thereafter, the temperature of the reflux condenser is raised to -2O 0 C to remove the trifluoromethylsulfonyl fluoride, CF 3 SO 2 F, which is formed in the reaction.
• 4.2 g (20 mmol) of rubidium iodide and 24.2 g (200 mmol) of allyl bromide are added to the remaining suspension of RbOCF 3 and the reaction mixture is stirred at 60 ° C. for 61 hours.
• Trifluoromethylsulfonylfluoride CF 3 SO 2 F, remove within 30 min.
• Reaction mixture is stirred for 1 hour at 0 ° C. Thereafter, the temperature of the reflux condenser is raised to room temperature to remove the trifluoromethylsulfonyl fluoride, CF 3 SO 2 F, formed in the reaction within 30 minutes. 5 ml of dry dimethylformamide and 3.73 g (17.2 mmol) of 3-Brompropylmesylat from Example 7d) are added to the remaining in the flask suspension of RbOCF 3 at 0 ° C bath temperature and the reaction mixture is 15 hours at 50 0 C and 23 hours at 60 ° C stirred.
• the product, 1-bromo-3- (trifluoromethoxy) propane is characterized by 1 H and 19 F NMR spectra.
• the NMR data for the product, 1-bromo-3- (trifluoromethoxy) propane, are identical to the data described in Example 7c).
• hex-5-enyl triflate (116 g) is not further purified but stored at -78 ° C and further reacted as crude product (Example 8b).
• the yield of hex-5-enyl triflate is 88.5% based on hex-5-en-1-ol.
• the product, hex-5-enyl triflate is characterized by 1 H NMR spectrum.
• the yield of 1-trifluoromethoxy-hex-5-ene is 43%, based on hex-5-enyl triflate.
• the product, 1-trifluoromethoxy-hex-5-ene is characterized by 1 H and 19 F NMR spectra.
• Triethylammonium chloride is filtered off and washed several times with ethyl acetate.
• the combined filtrates are concentrated to about 600 ml and washed with 75 ml of 10% hydrochloric acid, with 50 ml of saturated Nathumhydrogencarbonatives and with 50 ml of saturated sodium chloride solution.
• the organic phase is on
• Reaction mixture is stirred for 1 hour at 0 0 C on. Thereafter, the temperature of the reflux condenser is raised to room temperature, at T / EP2009 / 003177
• the product, 1-trifluoromethoxy-hex-5-ene is characterized by 1 H and 19 F NMR spectra.
• the NMR data for the product, 1-trifluoromethoxy-hex-5-ene, are identical to the data in Example 8b).
• the combined filtrates are concentrated to about 500 ml and washed with 50 ml of 10% hydrochloric acid, 50 ml of saturated sodium bicarbonate solution and 50 ml of saturated sodium chloride solution.
• the solvents are removed by means of a rotary evaporator.
• the residue is dissolved in 200 ml of dichloromethane and dried with MgSO 4 .
• the solution is filtered and dichloromethane evaporated.
• the crude product obtained is fractionally distilled in vacuo at 0.03 mbar. 97.7 g of dec-9-enyl mesylate obtained (boiling point: 103 0 C / 0.03 mbar).
• dec-9-enyl mesylate The yield of dec-9-enyl mesylate is 88%, based on dec-9-en-1-ol.
• the product, dec-9-enyl mesylate is characterized by a 1 H NMR spectrum.
• 1 H NMR solvent: CDCl 3 , reference substance: TMS
• ⁇ , ppm 1.22- 1.46 m (10H, 5CH 2 ), 1.72 quin (CH 2 ), 2.03 m (CH 2 ), 2.97 s (CH 3 ) , 4.19 t
• Example 11 1- (trifluoromethoxy) -butane, / 7-C 4 H 9 OCF 3
• Reaction mixture is stirred for 1 hour at 0 0 C on. Thereafter, the temperature of the reflux condenser is raised to room temperature to remove the trifluoromethylsulfonyl fluoride, CF 3 SO 2 F, formed in the reaction within 30 minutes.
• the temperature of the reflux condenser is raised to room temperature to remove the trifluoromethylsulfonyl fluoride, CF 3 SO 2 F, formed in the reaction within 30 minutes.
• To the remaining suspension of the piston RbOCF 3 15 ml of dry N, N-dimethylformamide, and 4:37 g (20.8 mmol) of di-n-butylsulfate at 0 ° C bath temperature and the reaction mixture is stirred for 72 hours at 70 0 C. Thereafter, all volatile products in a vacuum at 20 mbar and max. 50 ° C bath temperature in a cooled distillation trap (-196 0 C) condensed.
• Example 12 ⁇ - (Trifluoromethoxy) ethyl acetate, CF 3 OCH 2 C (O) OC 2 H 5
• Example 13a 2-Methylsulfonylacetic acid ethyl ester, (2-mesylacetic acid ethyl ester), CH 3 SO 2 OCH 2 C (O) OC 2 H 5
• the solid is rinsed once with 100 ml and twice with 200 ml of ethyl acetate.
• the combined filtrates are washed with 200 ml of water, twice with 100 ml of 10% hydrochloric acid, 100 ml of saturated sodium bicarbonate solution and 100 ml of saturated
• Example 13b ⁇ - (trifluoromethoxy) ethyl acetate, (2- (trifluoromethoxy) ethyl acetate), CF 3 OCH 2 C (O) OC 2 H 5
• the temperature of the reflux condenser is raised to 5 room temperature to remove the trifluoromethylsulfonyl fluoride, CFaSO 2 F, which is formed in the reaction.
• CFaSO 2 F trifluoromethylsulfonyl fluoride
• Example 14 ⁇ - (trifluoromethoxy) ethyl acetate, (2- (trifluoromethoxy) ethyl acetate), CF 3 OCH 2 C (O) OC 2 H 5
• the product, 2- (trifluoromethoxy) - ethyl acetate is determined by 1 H and 19 F NMR spectra characterized.
• the NMR data for the product, 2- (trifluoromethoxy) -acetic acid ethyl ester, are identical to the data in Example 12.
• Example 15 1-Chloro-3- (trifluoromethoxy) propane, CICH 2 CH 2 CH 2 OCF 3 CICH 2 CH 2 CH 2 OSO 2 Cl + RbOCF 3 -> CICH 2 CH 2 CH 2 OCF 3 + RbOSO 2 Cl
• Reaction mixture is stirred for 1 hour at 0 0 C on. Thereafter, the temperature of the reflux condenser is raised to room temperature to remove the trifluoromethylsulfonyl fluoride, CF 3 SO 2 F, formed in the reaction within 30 minutes.
• the temperature of the reflux condenser is raised to room temperature to remove the trifluoromethylsulfonyl fluoride, CF 3 SO 2 F, formed in the reaction within 30 minutes.
• N-dimethylformamide and 18.2 g (92.8 mmol) of 5-Hexene-1-yl trifluoroacetate from Example 12 a) at 0 0 C bath temperature and the reaction mixture is 124 Stirred at 100 ° C to 120 ° C hours. Thereafter, all volatile products in a vacuum at 0.1 mbar and max.
• Reflux cooler which is cooled to -80 ° C, 39.2 g (179.8 mmol) of trifluoromethyl triflate, CF 3 SO 2 OCF 3 , added slowly with stirring and cooling the reaction mixture with a bath (0 ° C). The reaction mixture is further stirred for 1 hour at 0 ° C. Thereafter, the temperature of the reflux condenser is raised to room temperature to remove the trifluoromethylsulfonyl fluoride, CF 3 SO 2 F, formed in the reaction within 30 minutes.
• the crude product obtained (purity: 96%), i-trifluoromethoxy-dec-9-ene (26.6 g, yield: 91%).
• In the Vacuum distilled at 20 mbar (boiling point: 76 ° C / 20 mbar, 38 ° C / 1.5 mbar) .
• the product, 1-trifluoromethoxy-dec-9-ene is characterized by 1 H and 19 F NMR spectra.
• the NMR data for the product, 1-trifluoromethoxy-dec-9-ene are identical to the data in Example 10b).
• CH 2 CH (CH 2 ) SOSO 2 CH 3 + KOCF 3 ⁇
• CH 2 CH (CH 2 ) S OCF 3 + KOSO 2 CH 3
• Trifluoromethyl triflate, CF 3 SO 2 OCFs slowly added with stirring and cooling the reaction mixture with a bath (O 0 C). The reaction mixture is further stirred for 1 hour at 0 ° C. Thereafter, the temperature of the reflux condenser is raised to room temperature to remove the trifluoromethylsulfonyl fluoride, CF 3 SO 2 F, formed in the reaction within 30 minutes. 31 ml of dry N, N-dimethylacetamide and 2.9 g (11.9 mmol) of 2-butenyl-1,4-dimesylate from Example 15a) at 0 ° C.
• reaction mixture is cooled to room temperature, placed on ice and the organic phase is separated at 0 0 C.
• the aqueous phase is extracted with methyl tert-butyl ether (MTB ether) and the combined organic phases are washed with water. From this phase, the solvent is removed at 30 0 C in vacuo and the resulting product is chromatographed. It comes to a colorless, oily liquid.
• reaction mixture is added to 0.5 N HCl cooled to 0 ° C. and stirred for 1 hour. Then the separated organic phase and the aqueous phase extracted with methyl tert-butyl ether (MTB ether). The combined organic phases are washed with water and dried with Na 2 SO 4 . The solvent is removed at 30 0 C in vacuo and the resulting alcohol 5 is chromatographed. It comes to a colorless, oily liquid.
• MTB ether methyl tert-butyl ether
• Example 24 Ethyl 2-trifluoromethoxy-lactate, CF 3 OCH (CH 3 ) C (O) OC 2 H 5
• Example 25 2-Trifluoromethoxy-acetic acid sodium salt, (sodium 2-trifluoromethoxyacetate), CF 3 OCH 2 C (O) ONa
• the substance decomposes without melting above 200 ° C.
• the product sodium 2-trifluoromethoxyacetate, is characterized by 1 H and 19 F NMR spectra.
• NMR data 1 H NMR (solvent: DMSO-D 6 , reference substance: TMS), ⁇ , ppm: 4.1 I s (CH 2 ).
• Example 27 1-Trifluoromethoxy-hexan-6-ol, CF 3 OCH 2 (CH 2 ) 2 H 2 OH
• reaction mixture is cooled to room temperature and evacuated for 5 minutes at about 50 mbar. After venting, 3 ml of water, 3 ml of 3M sodium hydroxide solution and 3 ml of 30% strength hydrogen peroxide solution are added in succession. After stirring for one hour, the mixture is transferred to a separatory funnel and washed three times with n-pentane. The combined organic phases are dried with MgSO 4 and the pentane is removed after filtration on a rotary evaporator. This gives 3.48 g of a clear, colorless liquid whose composition is determined by means of 1 H-NMR to 93% product and 7% pentane.
• Diborane is generated as follows: 0.39 g (10.3 mmol) of sodium borohydride in 10 ml of diethylene glycol dimethyl ether are added dropwise to a solution of 2.95 g (20.8 mmol) of boron trifluoride etherate in 5 ml of diethyl ether in a 25 ml round bottom flask. After the dropwise addition and completion of gas evolution, the reaction mixture is heated for 1 hour at 60 0 C to produce the diborane to complete the reaction.
• Example 28 2- (trifluoromethoxy) acetophenone, CF 3 OCH 2 C (O) C 6 H 5
• the temperature of the reflux condenser is raised to room temperature to remove the trifluoromethylsulfonyl fluoride, CF 3 SO 2 F, which is formed in the reaction.
• CF 3 SO 2 F trifluoromethylsulfonyl fluoride
• To the remaining suspension of KOCF 3 are added 17.22 g (86.5 mmol) of 2-bromoacetophenone, BrCH 2 C (O) CeH 5 , and 1.54 g (9.3 mmol) of potassium iodide, and the reaction mixture is stirred for 92 hours at room temperature. Thereafter, the reaction mixture is filtered and the filter cake is rinsed three times with 50 ml of n-pentane.
• the filtrate is mixed with 50 ml of water and the organic phase is separated, washed twice with water and dried with MgSO 4 . Then the solution is filtered and the solvent is evaporated. The residue is fractionally distilled. (Boiling point: 51-52 ° C at 0.7 mbar). It will contain 8.1 g of liquid 2- (trifluoromethoxy) acetophenone (purity: 95%). The yield of 2- (trifluoromethoxy) acetophenone is 44% based on 2-bromoacetophenone. The product, 2- (trifluoromethoxy) acetophenone, is characterized by 1 H and 19 F NMR spectra.
• NMR data 1 H NMR (solvent: CD 3 CN, reference substance: TMS), ⁇ , ppm: 5.40 s (CH 2 ), 7.55 g (2H, meta-H, C 6 H 5 ), 7.68 g (1 H, para-H, C 6 H 5), 7.93 d (2H, ortho-H, C 6 H 5).

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