Hydrochloric Acid → 4-Bromo-3-(trifluoromethyl)benzeneacetic acid
Reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8]C#N)=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].S(=O)(=O)(O)O.[C:20](=[O:23])([O-])[O-:21].[Na+].[Na+].Cl>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:20]([OH:21])=[O:23])=[CH:4][C:3]=1[C:11]([F:12])([F:13])[F:14]Participants
6
Conditions
- Temperature
- 115 °C
Procedure
To a flask containing 2-(4-bromo-3-(trifluoromethyl)phenyl)acetonitrile 46-5 (880 mg, 3.3 mmol) were added water (4.5 mL) and dropwise concentrated sulfuric acid (4.5 mL). The reaction mixture was stirred at 115° C. for 4 hours. After cooled down to room temperature, the reaction mixture was poured into water (100 mL). The resulting solution was neutralized with powder sodium carbonate to pH 12, treated with 1N HCl aqueous solution to pH around 2, and extracted with dichloromethane (50 mL×3). The combined organic layers were washed with brine, dried over Na2SO4 and then taken to dryness by rotary evaporation give 2-(4-bromo-3-(trifluoromethyl)phenyl)acetic acid 46-6 as pale yellow solid. MS m/z 283.1 (M+1)
Workup
- temperatureAfter cooled down to room temperature
- extractionextracted with dichloromethane (50 mL×3)
- washThe combined organic layers were washed with brine
- dry with materialdried over Na2SO4
- customtaken to dryness by rotary evaporation
Sources & evidence
- ORD record
- ord-5959ba8f0d4542dda2f68b97e7da3a57
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09238646B2
Reaction notes
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