Potassium Acetate → 2-Bromo-3-nitrobenzyl acetate

A stirred solution of 2-bromo-1-bromomethyl-3-nitrobenzene (20.2 g, 0.0685 mole), potassium acetate (10.08 g, 0.103 mole), and tetrabutylammonium chloride (1.5 g) in 150 ml of acetonitrile was heated at reflux for six hours. The reaction mixture was cooled, filtered, and extracted with methylene chloride. The extract was evaporated to give a residue which was redissolved in methylene chloride and washed twice with 150 ml portions of saturated aqueous sodium chloride solution. The organic phase was passed through phase separation filter paper and evaporated to give a dark solid. The solid was purified by column chromatography on silica gel, elution with toluene, to give (2-bromo-3-nitrophenyl)methyl acetate as a yellow solid (9.6 g, mp 60°-63°).

1. temperatureat reflux for six hours
2. temperatureThe reaction mixture was cooled
3. filtrationfiltered
4. extractionextracted with methylene chloride
5. customThe extract was evaporated
6. customto give a residue which
7. washwashed twice with 150 ml portions of saturated aqueous sodium chloride solution
8. customThe organic phase was passed through phase separation
9. filtrationfilter paper
10. customevaporated
11. customto give a dark solid
12. customThe solid was purified by column chromatography on silica gel, elution with toluene

ORD record

ord-97a9a6e7eac0461b80c6b1e62078f6e4

Source dataset

uspto-grants-1985_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04536591