Boron tribromide → 2-(2,2,2-Trifluoro-1-hydroxyethyl)phenol

HRID 2387038Notes

Reaction equation

HRID 2387038 reaction equation
B(Br)(Br)Br.[F:5][C:6]([F:18])([F:17])[CH:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15]C)[OH:8]>ClCCl>[F:5][C:6]([F:17])([F:18])[CH:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[OH:15])[OH:8]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 28292482,2,2-Trifluoro-1-(2-methoxyphenyl)ethanol

Product 1

HCID 28292952-(2,2,2-Trifluoro-1-hydroxyethyl)phenolYield 107.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boron tribromide (10 ml) (1M soln in DCM) was added to a solution of 2,2,2-trifluoro-1-(2-methoxyphenyl)ethanol (1.5 g) in dichloromethane (20 ml). The reaction mixture was stirred at room temperature under a atmosphere of nitrogen for 56 hrs. The mixture was then partitioned between DCM (100 ml) and 1N HCl (100 ml), organics washed with water (100 ml), dried over magnesium sulfate, filtered and solvent removed in vacuo to afford the title compound as a clear yellow oil (1.5 g). 1H NMR (CDCl3): δ 3.50 (bs, 1H), 5.25 (m, 1H), 6.73 (bs, 1H), 7.00 (m, 2H), 7.32 (d, J=2.56 Hz, 1H), 7.45 (m, 1H).

Workup

  1. customThe mixture was then partitioned between DCM (100 ml) and 1N HCl (100 ml)
  2. washorganics washed with water (100 ml)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customsolvent removed in vacuo

Sources & evidence

ORD record
ord-f5c96b6bbef14d55bb25d32df5afbf83
Source dataset
uspto-grants-2012_09
Patent number
US08268835B2

Reaction notes

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