Water → 4,5-Difluoro-2-(2-hydroxyethyl)phenol

HRID 921183Notes

Reaction equation

HRID 921183 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][C:5]([CH2:9][CH2:10][OH:11])=[C:4]([O:12]C)[CH:3]=1.B(Br)(Br)Br.O>C(Cl)Cl>[F:8][C:7]1[C:2]([F:1])=[CH:3][C:4]([OH:12])=[C:5]([CH2:9][CH2:10][OH:11])[CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromideHCID 552676712-(4,5-Difluoro-2-methoxyphenyl)ethan-1-ol

Product 1

HCID 1172770664,5-Difluoro-2-(2-hydroxyethyl)phenolYield 60.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-(4,5-difluoro-2-methoxyphenyl)ethanol (800 mg, 4.25 mmol) in DCM (25 mL) at 0° C. was added 1M BBr3 (17.01 mL, 17.01 mmol) solution and the resulting mixture was allowed to warm to room temp and stir for 4 h. Then, water (dropwise) was added and after the bubbling stops mixture was diluted with DCM and washed with water, dried (Na2SO4), filtered and concentrated. The residue was then purified by Biotage (5-70%, EtOAc/hexane) to afford 4,5-difluoro-2-(2-hydroxyethyl)phenol (450 mg, 2.58 mmol, 60.8% yield) as clear viscous oil. 1H NMR (500 MHz, CDCl3) δ 6.93-6.84 (m, 1H), 6.75 (dd, J=11.5, 7.1 Hz, 1H), 4.03-3.96 (m, 2H), 2.85 (t, J=5.2 Hz, 2H).

Workup

  1. washwashed with water
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was then purified by Biotage (5-70%, EtOAc/hexane)

Sources & evidence

ORD record
ord-e94c622d01e140b6923e1a72f55afadc
Source dataset
uspto-grants-2016_03
Patent number
US09273067B2

Reaction notes

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