Water → 2-Bromo-4-(trifluoromethoxy)phenol

HRID 1420682Notes

Reaction equation

HRID 1420682 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

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

  1. washthe organic phase was washed with water (400 ml), brine (200 ml)
  2. dry with materialdried (MgSO4)
  3. customThe solvent was removed
  4. 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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