Methanol → Methyl 4-fluoro-3-(trifluoromethyl)benzoate
Reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].O=S(Cl)Cl.[CH3:19]O>>[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([O:8][CH3:19])=[O:7])=[CH:4][C:3]=1[C:11]([F:12])([F:13])[F:14]Participants
4
Conditions
- Temperature
- 5 °C
Procedure
35.4 g (170 mmol) of 4-fluoro-3-(trifluoromethyl)-benzoic acid in 250 ml of methanol are mixed with 68 ml of SOCl2, whilst cooling with ice, at 5° C. within 25 minutes. After it has all been added, the reaction mixture is refluxed for a further 3 hours. The reaction solution is cooled to ambient temperature and evaporated down in vacuo. The oily residue is taken up in 200 ml of diethylether and extracted with water, saturated NaHCO3 solution and again with water. The combined organic phases are dried over magnesium sulphate and evaporated down in vacuo.
Workup
- additionall been added
- temperaturethe reaction mixture is refluxed for a further 3 hours
- temperatureThe reaction solution is cooled to ambient temperature
- customevaporated down in vacuo
- extractionextracted with water, saturated NaHCO3 solution and again with water
- dry with materialThe combined organic phases are dried over magnesium sulphate
- customevaporated down in vacuo
Sources & evidence
- ORD record
- ord-94e293ef396944d5adc3ac4ec7a20682
- Source dataset
- uspto-grants-2001_11
- Patent number
- US06323207B1
Reaction notes
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