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

HRID 580836Notes

Reaction equation

HRID 580836 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) ware added and the organic phase was washed further with water (400 ml), brine (200 ml) and dried (MgSO4). The solvent was removed and the residue was purified by distillation at reduced pressure to give the title compound. 1H NMR (250 MHz, CDCl3) δ 7.38 (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

  1. washthe organic phase was washed further with water (400 ml), brine (200 ml)
  2. dry with materialdried (MgSO4)
  3. customThe solvent was removed
  4. distillationthe residue was purified by distillation at reduced pressure

Sources & evidence

ORD record
ord-cc5e1f9aca214d949d3e24baa86dae86
Source dataset
uspto-grants-1999_07
Patent number
US05919781

Reaction notes

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