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

HRID 858680Notes

Reaction equation

HRID 858680 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-0e5420eaf6664f1f9790cac90709b43d
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

Loading…