Water → 3,4-Difluoro-2-(2-hydroxyethyl)phenol

HRID 921176Notes

Reaction equation

HRID 921176 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([O:9]C)[C:3]=1[CH2:11][CH2:12][OH:13].O>C(Cl)Cl>[F:1][C:2]1[C:3]([CH2:11][CH2:12][OH:13])=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 2

HCID 962WaterHCID 1172810202-(2,3-Difluoro-6-methoxyphenyl)ethanol

Product 1

HCID 1172770673,4-Difluoro-2-(2-hydroxyethyl)phenolYield 67.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-(2,3-difluoro-6-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. Water (dropwise) was then 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 (5-50%, EtOAc/hexane) to afford 3,4-difluoro-2-(2-hydroxyethyl)phenol (500 mg, 2.87 mmol, 67.5% yield) as clear viscous oil. 1H NMR (500 MHz, CDCl3) δ 7.85 (br. s., 1H), 7.04-6.93 (m, 1H), 6.71-6.60 (m, 1H), 4.07-4.01 (m, 2H), 3.04-2.95 (m, 2H), 2.38 (br. s., 1H).

Workup

  1. washwashed with water
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was then purified by Biotage (5-50%, EtOAc/hexane)

Sources & evidence

ORD record
ord-fff5081485734476883d4ce21746a562
Source dataset
uspto-grants-2016_03
Patent number
US09273067B2

Reaction notes

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