Methanol → 2-Fluoro-4-(2-hydroxyethyl)phenol
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
Product 1
Reagents, catalysts & solvents 1
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
- concentrationwas concentrated under reduced pressure
- customThe residue was partitioned between EtOAc (800 mL) and water (100 mL)
- customThe organic layer was dried
- concentrationconcentrated to dryness
Sources & evidence
- ORD record
- ord-96fe742a6f6944548b58cbf634560b95
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09273054B2
Reaction notes
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