Methanol → 2-Fluoro-4-(2-hydroxyethyl)phenol

HRID 920346

Reaction equation

HRID 920346 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10](O)=[O:11])[CH:5]=[CH:6][C:7]=1[OH:8].B.CO>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][OH:11])[CH:5]=[CH:6][C:7]=1[OH:8]

Participants

5

Reactant 3

HCID 887MethanolHCID 6331BoraneHCID 680143-Fluoro-4-hydroxybenzeneacetic acid

Product 1

HCID 451190812-Fluoro-4-(2-hydroxyethyl)phenolYield 94.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(3-fluoro-4-hydroxyphenyl)acetic acid (9.8 g, 57.6 mmol) in THF (500 mL) was added dropwise 57.6 mL of borane (10M in Me2S) at room temperature. The reaction mixture was stirred at room temperature for 12 hours. The reaction mixture was added to CH3OH and was concentrated under reduced pressure. The residue was partitioned between EtOAc (800 mL) and water (100 mL). The organic layer was dried and concentrated to dryness to give the title product (8.5 g, 76%).

Workup

  1. concentrationwas concentrated under reduced pressure
  2. customThe residue was partitioned between EtOAc (800 mL) and water (100 mL)
  3. customThe organic layer was dried
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-96fe742a6f6944548b58cbf634560b95
Source dataset
uspto-grants-2016_03
Patent number
US09273054B2

Linked notes

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