Butyl bromide → 1-Bromo-4-(butoxymethyl)benzene

Temperature

0 °C

To a solution of 4-bromobenzyl alcohol (10.0 g, 53.5 mmol) in N,N-dimethylformamide (200 mL) was added sodium hydride (3.08 g, 64.2 mmol, 50% in oil) at 0° C. This mixture was stirred for 5 minutes at 0° C., and 1-bromobutane (7.47 mL, 69.3 mmol) was added thereto at 0° C. This mixture was stirred for 40 minutes at room temperature and then stirred for 25 minutes at 70° C. The reaction solution was partitioned into water and ethyl acetate at 0° C. The organic layer was washed with water and saturated aqueous sodium chloride, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under a reduced pressure. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=20:1) to obtain the title compound (11.5 g, 89%).

1. customat 0° C
2. stirringThis mixture was stirred for 40 minutes at room temperature
3. stirringstirred for 25 minutes at 70° C
4. customThe reaction solution was partitioned into water and ethyl acetate at 0° C
5. washThe organic layer was washed with water and saturated aqueous sodium chloride
6. dry with materialdried over anhydrous magnesium sulfate
7. customthe solvent was evaporated under a reduced pressure
8. customThe residue was purified by silica gel column chromatography (heptane:ethyl acetate=20:1)

ORD record

ord-c867eb8cb16542a4bd9127ec7ee7dbb3

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08841327B2