Water → 2-Bromo-4-(trifluoromethoxy)phenol
Reaction equation
[Br:1]Br.[F:3][C:4]([F:14])([F:13])[O:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.ClCCl.O>C(Cl)(Cl)Cl>[Br:1][C:8]1[CH:7]=[C:6]([O:5][C:4]([F:13])([F:14])[F:3])[CH:11]=[CH:10][C:9]=1[OH:12]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of bromine (32 g, 0.2 mol) in chloroform (50 mL) was added dropwise to a stirred, cooled (0° C.) solution of 4-(trifluoromethoxy)phenol (35.6 g, 0.2 mol) in chloroform (280 mL). The mixture was stirred at 0° C. for 1 h. and at room temperature for 2 h. Dichloromethane (200 mL) and water (400 mL) were added and the layers were separated. The organic fraction was washed with water (400 mL) and brine (200 mL), dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by distillation under reduced pressure to give the title compound as a colorless oil. 1H NMR (250 MHz, CDCl3) δ7.38 (1H, d, J 2.1 Hz), 7.13 (1H, dd, J 9.1, 2.1 Hz), 7.03 (1H, d, J 9.1 Hz), and 5.53 (1H, s).
Workup
- customthe layers were separated
- washThe organic fraction was washed with water (400 mL) and brine (200 mL)
- dry with materialdried (MgSO4)
- customthe solvent was evaporated under reduced pressure
- distillationThe residue was purified by distillation under reduced pressure
Sources & evidence
- ORD record
- ord-cf719c9137384c1ab97b59e3a331f9f0
- Source dataset
- uspto-grants-2003_02
- Patent number
- US06518273B1
Reaction notes
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