(Dimethyl sulfide)trihydroboron → 2-(3-(Bromomethyl)-5-fluorophenyl)ethanol
Reaction equation
CSC.B.[Br:5][CH2:6][C:7]1[CH:8]=[C:9]([CH2:14][C:15](O)=[O:16])[CH:10]=[C:11]([F:13])[CH:12]=1>C1COCC1>[Br:5][CH2:6][C:7]1[CH:8]=[C:9]([CH2:14][CH2:15][OH:16])[CH:10]=[C:11]([F:13])[CH:12]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
Borane dimethyl sulfide complex (2M in THF, 26.3 mL) was added dropwise over 10 minutes to a solution of 2-(3-(bromomethyl)-5-fluorophenyl)acetic acid [Aromatic Intermediate 4, step a] (6.5 g) in THF (120 mL) at 0° C. The mixture was stirred at 0° C. for 10 minutes and then at 20° C. for 1 hour. The reaction mixture was quenched by dropwise addition of methanol and the solvents were removed under reduced pressure. The crude product was purified by flash silica chromatography using 30% ethyl acetate in isohexane. Fractions containing the product were concentrated to dryness to afford the titled compound. Yield 4.70 g.
Workup
- waitat 20° C. for 1 hour
- customThe reaction mixture was quenched by dropwise addition of methanol
- customthe solvents were removed under reduced pressure
- customThe crude product was purified by flash silica chromatography
- additionFractions containing the product
- concentrationwere concentrated to dryness
Sources & evidence
- ORD record
- ord-fcabc19157d144a8a8f0082cab8725a8
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08476265B2
Reaction notes
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