1-(4-Bromophenyl)cyclobutane-1-carboxylic acid → (1-(4-Bromophenyl)cyclobutyl)methanol

To a solution of 1-(4-bromophenyl)cyclobutanecarboxylic acid (300 mg, 1.20 mmol) in 1,4-dioxane (5 mL) was added borane dimethylsulfide complex (0.24 mL, 2.4 mmol) dropwise at 0° C. The ice bath was removed, and the reaction mixture was stirred at room temperature for 10 min. The reaction mixture was quenched with methanol (20 mL). The organic solvents were removed under reduced pressure to give a residue, which was dissolved in ethyl acetate, then washed with brine. The organic phase was concentrated to give [1-(4-bromophenyl)cyclobutyl]methanol (170 mg, 62% yield) as a yellow oil which was used directly in the next step.

1. customThe ice bath was removed
2. customThe reaction mixture was quenched with methanol (20 mL)
3. customThe organic solvents were removed under reduced pressure
4. customto give a residue, which
5. washwashed with brine
6. concentrationThe organic phase was concentrated

ORD record

ord-02cdec2d774246288b2abeba53c2dde3

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08889730B2