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

HRID 1453131Notes

Reaction equation

HRID 1453131 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 stirres 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 vacuuo 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. customat room temperature
  2. customfor 56 hrs
  3. customThe mixture was then partitioned between DCM (100 ml) and 1N HCl (100 ml)
  4. washorganics washed with water (100 ml)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customsolvent removed in vacuuo

Sources & evidence

ORD record
ord-f7f8722b2bfa4867b7235030d4448f8f
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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