Carbon Tetrachloride → Methyl 2-(bromomethyl)-3-nitrobenzoate

A mixture of 100.0 g of methyl 2-methyl-3-nitrobenzoate, 100.0 g of N-bromosuccinimide, 3.0 g of dibenzoyl peroxide and 1000 ml of carbon tetrachloride was refluxed for 24 hours. The reaction mixture was cooled, 3.0 g of dibenzoyl peroxide added, and refluxing continued an additional 24 hours. The reaction mixture was cooled, filtered and the filtrate concentrated in vacuo. The crude reaction product was dissolved in ether and the organic solution washed sequentially with saturated sodium sulfite (500 ml), water (2×500 ml), 2.5% sodium hydroxide (500 ml), water (2×500 ml) and saturated brine (500 ml). The organic solution was dried over magnesium sulfate, filtered and the solvent evaporated in vacuo giving a pale yellow oily solid. Recrystalllization from 350 ml of 1-chlorobutane/cyclohexane (2:1) gave 73.9 g of methyl 2-bromomethyl-3-nitrobenzoate, m.p. 67°-70°.

1. temperaturewas refluxed for 24 hours
2. temperatureThe reaction mixture was cooled
3. temperaturerefluxing
4. temperatureThe reaction mixture was cooled
5. filtrationfiltered
6. concentrationthe filtrate concentrated in vacuo
7. customThe crude reaction product
8. washthe organic solution washed sequentially with saturated sodium sulfite (500 ml), water (2×500 ml), 2.5% sodium hydroxide (500 ml), water (2×500 ml) and saturated brine (500 ml)
9. dry with materialThe organic solution was dried over magnesium sulfate
10. filtrationfiltered
11. customthe solvent evaporated in vacuo
12. customgiving a pale yellow oily solid

ORD record

ord-1aa257d84f0a42fc9e249dbfb9ff3317

Source dataset

uspto-grants-1987_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04687508