Methyl iodide → 1-Bromo-4-(methoxymethyl)benzene

Temperature

0 °C

To a suspension of 60% sodium hydride (1.6 g) in dimethylformamide (50 ml) was added 4-bromobenzyl alcohol (5.00 g) under ice-water cooling and the mixture was stirred at 0° C. for 0.5 hour. To the mixture was added methyl iodide (2 ml) under ice-water cooling and the mixture was stirred at 0° C. for 1 hour. The mixture was partitioned between ethyl acetate and water. The organic layer was separated, washed with water and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by silica gel column chromatography eluting with hexane to give 4-(methoxymethyl)bromobenzene as colorless oil (3.63 g).

1. stirringthe mixture was stirred at 0° C. for 1 hour
2. customThe mixture was partitioned between ethyl acetate and water
3. customThe organic layer was separated
4. washwashed with water and brine
5. dry with materialdried over magnesium sulfate
6. customevaporated in vacuo
7. customThe residue was purified by silica gel column chromatography
8. washeluting with hexane

ORD record

ord-570b6370c97d4827984aac533c2b9aeb

Source dataset

uspto-grants-2005_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06967197B2