Benzyl Chloride → 2-(Benzyloxy)-4-bromo-6-nitroaniline

Temperature

80 °C

To a suspension of 50 g (325 mmol) 2-amino-nitrophenol, 45 g (325 mmol) potassium carbonate and 2 g (13 mmol) sodium iodide in 400 ml ethanol were added 47 ml (408 mmol) benzyl chloride and the mixture was heated to 80° C. After 2 h, the reaction mixture was cooled down and the solvent was evaporated. The residue was dissolved in ethyl acetate and extracted with water. The organic layer was dried over anhydrous magnesium sulphate and evaporated. Coevaporation with dichloromethane (three times) led to a dark brown oily residue which was dissolved in 400 ml acetonitrile. After addition of 63.4 g (356 mmol) N-bromosuccinimide, the reaction mixture was refluxed for 1 h. After cooling down, 400 g silica gel were added and the mixture was evaporated to dryness. The resulting solid was put on a column and the product was eluted with ethyl acetate/light petroleum ether (4:1). Evaporation of the eluent afforded a solid which was recrystallized from ethyl acetate/heptane to give 62 g (59%) of the title compound as a red solid. m.p. 90° C.

1. temperaturethe reaction mixture was cooled down
2. customthe solvent was evaporated
3. dissolutionThe residue was dissolved in ethyl acetate
4. extractionextracted with water
5. dry with materialThe organic layer was dried over anhydrous magnesium sulphate
6. customevaporated
7. dissolutionwas dissolved in 400 ml acetonitrile
8. temperaturethe reaction mixture was refluxed for 1 h
9. temperatureAfter cooling down
10. addition400 g silica gel were added
11. customthe mixture was evaporated to dryness
12. washthe product was eluted with ethyl acetate/light petroleum ether (4:1)
13. customEvaporation of the eluent
14. customafforded a solid which
15. customwas recrystallized from ethyl acetate/heptane

ORD record

ord-cf44212ac6b84f358f15ea72bb56f3e8

Source dataset

uspto-grants-2007_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07307084B2