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

HRID 1420806Notes

Reaction equation

HRID 1420806 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>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

5

Conditions

Temperature
0 °C

Procedure

To a cooled (0° ) 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 h. and at room temperature for 2 h. Dichloromethane (200 ml) and waster (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) 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

  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-577d905298b5464983bb4ea1b3f8e734
Source dataset
uspto-grants-2000_06
Patent number
US06071927

Reaction notes

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