Carbon Dioxide → 2-Chloro-4-(trifluoromethoxy)benzoic acid
Reaction equation
C([Li])CCC.[Cl:6][C:7]1[CH:12]=[C:11]([O:13][C:14]([F:17])([F:16])[F:15])[CH:10]=[CH:9][C:8]=1Br.[C:19](=[O:21])=[O:20]>CCOCC>[Cl:6][C:7]1[CH:12]=[C:11]([O:13][C:14]([F:17])([F:16])[F:15])[CH:10]=[CH:9][C:8]=1[C:19]([OH:21])=[O:20]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
n-Butyllithium (2.5M in hexane, 38 ml) was added to a stirred, cooled solution of 2-chloro-4-trifluoromethoxybromobenzene (25 g) in ether while maintaining the temperature below -70° C. The mixture was stirred at -78° C. for 4 hours then poured onto solid carbon dioxide with stirring. The mixture was allowed to warm to room temperature and acidified to pH1. The layers were separated and the organic layer was washed with water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was triturated with cyclohexane and filtered to give 2-chloro-4-trifluoromethoxybenzoic acid as a white solid mp 90.6°-91.2° C.
Workup
- temperaturewhile maintaining the temperature below -70° C
- stirringwith stirring
- temperatureto warm to room temperature
- customThe layers were separated
- washthe organic layer was washed with water
- dry with materialdried (MgSO4)
- filtrationfiltered
- customThe filtrate was evaporated to dryness
- customthe residue was triturated with cyclohexane
- filtrationfiltered
Sources & evidence
- ORD record
- ord-3587d7e5bc8d45138440fe9800bfdd2f
- Source dataset
- uspto-grants-1997_08
- Patent number
- US05656573
Reaction notes
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