Water → 2-Bromo-4-(trifluoromethoxy)phenol
Reaction equation
[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[Br:13]Br.ClCCl.O>C(Cl)(Cl)Cl>[Br:13][C:6]1[CH:5]=[C:4]([O:3][C:2]([F:11])([F:12])[F:1])[CH:9]=[CH:8][C:7]=1[OH:10]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a cooled (0° C.) solution of 4-trifluoromethoxyphenol (35.6 g, 0.2 mol) in chloroform (280 ml) was added dropwise a solution of bromine (32 g, 0.2 mol) in chloroform (50 ml). The solution was stirred at 0° C. for 1 hour and at room temperature for 2 hours. Dichloromethane (200 ml) and water (400 ml) were added and the organic phase was washed with water (400 ml), brine (200 ml) and dried (MgSO4). The solvent was removed and the residue purified by distillation at reduced pressure to give the title compound; δH (250MHz, CDCl3) 7.38 (1H, d, J 2.1Hz, 3-H), 7.13 (1H, dd, J 9.1, 2.1Hz, 5-H), 7.03 (1H, d, J 9.1Hz, 6-H), 5.53 (1H, s, ArOH).
Workup
- washthe organic phase was washed with water (400 ml), brine (200 ml)
- dry with materialdried (MgSO4)
- customThe solvent was removed
- distillationthe residue purified by distillation at reduced pressure
Sources & evidence
- ORD record
- ord-2728777ca32b4afdbbc7c89bd13a48b6
- Source dataset
- uspto-grants-2000_06
- Patent number
- US06071928
Reaction notes
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