Hexane → 2-Bromo-5-methoxybenzyl bromide

To a solution of above-described crude 1-(bromomethyl)-3-methoxybenzene (152.5 g) in 1 L of chloroform a solution of 134 g (0.841 mol) of bromine in 200 ml of chloroform was added dropwise by vigorous stirring at room temperature. The reaction mixture was stirred overnight at ambient temperature and then evaporated to dryness. The residue was triturated with 1000 ml of n-hexane, and the precipitate was filtered off, washed with 100 ml of n-hexane, and then dried in vacuum. An additional amount of the product was obtained by evaporation of mother liquor followed by treatment of the residue with 200 ml of n-hexane. In total, this procedure gave 153 g (55% overall yield for two stages) of 1-bromo-2-(bromomethyl)-4-methoxybenzene. (average of two runs)

1. stirringThe reaction mixture was stirred overnight at ambient temperature
2. customevaporated to dryness
3. customThe residue was triturated with 1000 ml of n-hexane
4. filtrationthe precipitate was filtered off
5. washwashed with 100 ml of n-hexane
6. customdried in vacuum
7. customAn additional amount of the product was obtained by evaporation of mother liquor

ORD record

ord-06529ac9ae0a4d9cb5293fee4379941e

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09187583B2