DE2122254A1 - Deuterierungsverfahren - Google Patents
DeuterierungsverfahrenInfo
- Publication number
- DE2122254A1 DE2122254A1 DE19712122254 DE2122254A DE2122254A1 DE 2122254 A1 DE2122254 A1 DE 2122254A1 DE 19712122254 DE19712122254 DE 19712122254 DE 2122254 A DE2122254 A DE 2122254A DE 2122254 A1 DE2122254 A1 DE 2122254A1
- Authority
- DE
- Germany
- Prior art keywords
- bromide
- alicyclic
- tertiary
- acyclic
- dbr
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 17
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 18
- 125000002015 acyclic group Chemical group 0.000 claims description 16
- 125000002723 alicyclic group Chemical group 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 9
- 239000011541 reaction mixture Substances 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- 239000002243 precursor Substances 0.000 claims description 5
- 239000007858 starting material Substances 0.000 claims description 5
- XLYOFNOQVPJJNP-ZSJDYOACSA-N Heavy water Chemical compound [2H]O[2H] XLYOFNOQVPJJNP-ZSJDYOACSA-N 0.000 claims description 4
- 125000004431 deuterium atom Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 230000002378 acidificating effect Effects 0.000 claims 1
- 125000002008 alkyl bromide group Chemical group 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 150000001925 cycloalkenes Chemical class 0.000 claims 1
- -1 alicyclic bromides Chemical class 0.000 description 18
- 239000000047 product Substances 0.000 description 11
- 150000001347 alkyl bromides Chemical class 0.000 description 5
- 125000004429 atom Chemical group 0.000 description 5
- BRTFVKHPEHKBQF-UHFFFAOYSA-N bromocyclopentane Chemical compound BrC1CCCC1 BRTFVKHPEHKBQF-UHFFFAOYSA-N 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 description 4
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 229910052805 deuterium Inorganic materials 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000001260 acyclic compounds Chemical class 0.000 description 2
- 150000001334 alicyclic compounds Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- AQIXEPGDORPWBJ-UHFFFAOYSA-N pentan-3-ol Chemical compound CCC(O)CC AQIXEPGDORPWBJ-UHFFFAOYSA-N 0.000 description 2
- QBUKAFSEUHGMMX-MTJSOVHGSA-N (5z)-5-[[3-(1-hydroxyethyl)thiophen-2-yl]methylidene]-10-methoxy-2,2,4-trimethyl-1h-chromeno[3,4-f]quinolin-9-ol Chemical compound C1=CC=2NC(C)(C)C=C(C)C=2C2=C1C=1C(OC)=C(O)C=CC=1O\C2=C/C=1SC=CC=1C(C)O QBUKAFSEUHGMMX-MTJSOVHGSA-N 0.000 description 1
- VLKZOEOYAKHREP-MICDWDOJSA-N 1-deuteriohexane Chemical compound [2H]CCCCCC VLKZOEOYAKHREP-MICDWDOJSA-N 0.000 description 1
- CAKWRXVKWGUISE-UHFFFAOYSA-N 1-methylcyclopentan-1-ol Chemical compound CC1(O)CCCC1 CAKWRXVKWGUISE-UHFFFAOYSA-N 0.000 description 1
- NAMYKGVDVNBCFQ-WFGJKAKNSA-N 2-bromo-1,1,1,3,3,3-hexadeuteriopropane Chemical compound [2H]C([2H])([2H])C(Br)C([2H])([2H])[2H] NAMYKGVDVNBCFQ-WFGJKAKNSA-N 0.000 description 1
- NEBYCXAKZCQWAW-UHFFFAOYSA-N 2-bromohexane Chemical compound CCCCC(C)Br NEBYCXAKZCQWAW-UHFFFAOYSA-N 0.000 description 1
- BDCFWIDZNLCTMF-UHFFFAOYSA-N 2-phenylpropan-2-ol Chemical compound CC(C)(O)C1=CC=CC=C1 BDCFWIDZNLCTMF-UHFFFAOYSA-N 0.000 description 1
- VTOQFOCYBTVOJZ-UHFFFAOYSA-N 3-bromopentane Chemical compound CCC(Br)CC VTOQFOCYBTVOJZ-UHFFFAOYSA-N 0.000 description 1
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 1
- XKIRHOWVQWCYBT-UHFFFAOYSA-N 3-ethylpentan-3-ol Chemical compound CCC(O)(CC)CC XKIRHOWVQWCYBT-UHFFFAOYSA-N 0.000 description 1
- 125000004136 7-norbornyl group Chemical group [H]C1([H])C([H])([H])C2([H])C([H])([H])C([H])([H])C1([H])C2([H])* 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 229910014033 C-OH Inorganic materials 0.000 description 1
- PGTANUNIOXCVLE-UHFFFAOYSA-N CC.[Br] Chemical compound CC.[Br] PGTANUNIOXCVLE-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 229910014570 C—OH Inorganic materials 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000003796 beauty Effects 0.000 description 1
- SXDBWCPKPHAZSM-UHFFFAOYSA-N bromic acid Chemical compound OBr(=O)=O SXDBWCPKPHAZSM-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B31/00—Reduction in general
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C23/00—Compounds containing at least one halogen atom bound to a ring other than a six-membered aromatic ring
- C07C23/02—Monocyclic halogenated hydrocarbons
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA082,325A CA962283A (en) | 1970-05-08 | 1970-05-08 | Process for deuterating bromide derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2122254A1 true DE2122254A1 (de) | 1971-11-18 |
Family
ID=4086771
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712122254 Pending DE2122254A1 (de) | 1970-05-08 | 1971-05-05 | Deuterierungsverfahren |
Country Status (6)
| Country | Link |
|---|---|
| CA (1) | CA962283A (enrdf_load_html_response) |
| CH (1) | CH561160A5 (enrdf_load_html_response) |
| DE (1) | DE2122254A1 (enrdf_load_html_response) |
| FR (1) | FR2091379A5 (enrdf_load_html_response) |
| GB (1) | GB1311423A (enrdf_load_html_response) |
| SE (1) | SE373354B (enrdf_load_html_response) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1236483A (en) * | 1984-03-19 | 1988-05-10 | Commonwealth Of Australia (The) | Labelling of organic molecules |
| JP2007528859A (ja) | 2003-07-24 | 2007-10-18 | 富士フイルム株式会社 | 重水素化（メタ）アクリル酸ノルボルニル、その製造法、その重合体、及び光学部材 |
| CN115215714B (zh) * | 2022-06-29 | 2023-08-18 | 理道新材(北京)科技有限公司 | 一种全氘代溴代环戊烷及其制备方法和应用 |
-
1970
- 1970-05-08 CA CA082,325A patent/CA962283A/en not_active Expired
-
1971
- 1971-05-03 GB GB1264671A patent/GB1311423A/en not_active Expired
- 1971-05-05 DE DE19712122254 patent/DE2122254A1/de active Pending
- 1971-05-07 CH CH680271A patent/CH561160A5/xx not_active IP Right Cessation
- 1971-05-07 FR FR7116698A patent/FR2091379A5/fr not_active Expired
- 1971-05-07 SE SE594671A patent/SE373354B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CH561160A5 (enrdf_load_html_response) | 1975-04-30 |
| CA962283A (en) | 1975-02-04 |
| GB1311423A (en) | 1973-03-28 |
| SE373354B (sv) | 1975-02-03 |
| FR2091379A5 (enrdf_load_html_response) | 1972-01-14 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |