Carbon Tetrachloride → 2-Bromo-5-methoxybenzyl bromide

To a solution of 173 g (0.86 mol) of 1-bromo-4-methoxy-2-methylbenzene in 850 ml of CCl4 153 g (0.86 mol) of NBS and 1.0 g of (PhCOO)2 were added at room temperature. This mixture was refluxed for 16 h, cooled to room temperature, and then filtered through glass frit (G2). The precipitate was additionally washed by 2×150 ml of CCl4. The combined filtrate was evaporated to dryness, and the residue was triturated with 600 ml of n-hexane. The precipitate was filtered off (G3 glass frit), washed by 50 ml of n-hexane, and dried in vacuum. This procedure gave 121 g of the title product. Additional amount of the product was obtained by evaporation of a mother liquor followed by crystallization of the residue from 200 ml of n-hexane at −25° C. In total, 157 g (65%; or 56% overall yield for two stages) of 1-bromo-2-(bromomethyl)-4-methoxybenzene has been isolated.

1. temperatureThis mixture was refluxed for 16 h
2. filtrationfiltered through glass frit (G2)
3. washThe precipitate was additionally washed by 2×150 ml of CCl4
4. customThe combined filtrate was evaporated to dryness
5. customthe residue was triturated with 600 ml of n-hexane
6. filtrationThe precipitate was filtered off (G3 glass frit)
7. washwashed by 50 ml of n-hexane
8. customdried in vacuum

ORD record

ord-a75f24e1e9b84fa3adadf2e9c083cfa1

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09187583B2