JPS55157530A - Preparation of 3-fluoro-4-phenylbenzaldehyde - Google Patents
Preparation of 3-fluoro-4-phenylbenzaldehydeInfo
- Publication number
- JPS55157530A JPS55157530A JP5919979A JP5919979A JPS55157530A JP S55157530 A JPS55157530 A JP S55157530A JP 5919979 A JP5919979 A JP 5919979A JP 5919979 A JP5919979 A JP 5919979A JP S55157530 A JPS55157530 A JP S55157530A
- Authority
- JP
- Japan
- Prior art keywords
- fluoro
- phenyltoluene
- hexamethylenetetramine
- flurbiprofen
- halide
- 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
- BBFKVFLWRKZSPM-UHFFFAOYSA-N 3-fluoro-4-phenylbenzaldehyde Chemical compound FC1=CC(C=O)=CC=C1C1=CC=CC=C1 BBFKVFLWRKZSPM-UHFFFAOYSA-N 0.000 title 1
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- ISXHZIQXRZTNKT-UHFFFAOYSA-N 2-fluoro-4-methyl-1-phenylbenzene Chemical compound FC1=CC(C)=CC=C1C1=CC=CC=C1 ISXHZIQXRZTNKT-UHFFFAOYSA-N 0.000 abstract 2
- -1 3-fluoro-4-phenylbenzyl halide Chemical class 0.000 abstract 2
- SYTBZMRGLBWNTM-UHFFFAOYSA-N flurbiprofen Chemical compound FC1=CC(C(C(O)=O)C)=CC=C1C1=CC=CC=C1 SYTBZMRGLBWNTM-UHFFFAOYSA-N 0.000 abstract 2
- 229960002390 flurbiprofen Drugs 0.000 abstract 2
- 239000004312 hexamethylene tetramine Substances 0.000 abstract 2
- 235000010299 hexamethylene tetramine Nutrition 0.000 abstract 2
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 2
- 239000011707 mineral Substances 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 230000003110 anti-inflammatory effect Effects 0.000 abstract 1
- 230000001754 anti-pyretic effect Effects 0.000 abstract 1
- IWLBIFVMPLUHLK-UHFFFAOYSA-N azane;formaldehyde Chemical compound N.O=C IWLBIFVMPLUHLK-UHFFFAOYSA-N 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 230000002140 halogenating effect Effects 0.000 abstract 1
- 230000026030 halogenation Effects 0.000 abstract 1
- 238000005658 halogenation reaction Methods 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
PURPOSE: To obtain the title compound, useful as the intermediate for the easy preparation of flurbiprofen, by the halogenation of 3-fluoro-4-phenyltoluene under specific conditions, followed by the reaction with hexamethylenetetramine and then hydrolysis with a mineral acid.
CONSTITUTION: 3-Fluoro-4-phenyltoluene is treated with 1.2W2.4mol equivalent, esp. 1.5W2.2mol equivalent, of a halogenating agent under radical conditions to give a mixture of 3-fluoro-4-phenylbenzyl halide and 3-fluoro-4-phenylbenzal halide, which is then treated with hexamethylenetetramine or ammonia-formaldehyde in a lower alcohol or lower aliphatic acid containing 30W70% H2O and subsequently hydrolyzed with a mineral acid to give the objective compound.
EFFECT: Flurbiprofen, having mild antiinflammatory, lenitive and antipyretic activities, is obtained via the title compound in a short process.
COPYRIGHT: (C)1980,JPO&Japio
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5919979A JPS55157530A (en) | 1979-05-16 | 1979-05-16 | Preparation of 3-fluoro-4-phenylbenzaldehyde |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5919979A JPS55157530A (en) | 1979-05-16 | 1979-05-16 | Preparation of 3-fluoro-4-phenylbenzaldehyde |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS55157530A true JPS55157530A (en) | 1980-12-08 |
Family
ID=13106508
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP5919979A Pending JPS55157530A (en) | 1979-05-16 | 1979-05-16 | Preparation of 3-fluoro-4-phenylbenzaldehyde |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS55157530A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011141974A (en) * | 2010-01-06 | 2011-07-21 | Tosoh F-Tech Inc | Nonaqueous electrolyte containing fluorine-containing phosphate ester-amide |
-
1979
- 1979-05-16 JP JP5919979A patent/JPS55157530A/en active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2011141974A (en) * | 2010-01-06 | 2011-07-21 | Tosoh F-Tech Inc | Nonaqueous electrolyte containing fluorine-containing phosphate ester-amide |
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