Carbon Tetrachloride → Methyl 2-(bromomethyl)-5-chlorobenzoate

Temperatur

80 °C

A mixture of methyl 5-chloro-2-methylbenzoate (3.13 g, 17.0 mmol), N-bromosuccinimide (3.17 g, 17.8 mmol), benzoyl peroxide (0.41 g, 1.70 mmol), and carbon tetrachloride (80 mL) was stirred at 80° C. for 16 h. After cooling to room temperature, the mixture was diluted with dichloromethane (200 mL) and washed with saturated sodium hydrogen carbonate aqueous (150 mL), and brine (150 mL). The organic layer was dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by flush column chromatography on silica gel eluting with hexane/ethyl acetate (60:1) to afford 1.13 g (25%) of the title compounds as colorless oil: 1H-NMR (CDCl3) δ 7.96 (1H, d, J=2.2 Hz), 7.46–7.40 (2H, m), 4.92 (2H, s), 3.96 (3H, s).

1. temperatureAfter cooling to room temperature
2. washwashed with saturated sodium hydrogen carbonate aqueous (150 mL), and brine (150 mL)
3. dry with materialThe organic layer was dried over magnesium sulfate
4. concentrationconcentrated under reduced pressure
5. customThe residue was purified
6. customby flush column chromatography on silica gel eluting with hexane/ethyl acetate (60:1)

ORD-Eintrag

ord-ab82ec7310024ad69875656afc842827

Quelldatensatz

uspto-grants-2007_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07238714B2