tert-Butyl 4-bromo-2-nitrobenzoate Chemical Properties

storage temp. 

Sealed in dry,Room Temperature

Appearance

Light yellow to yellow Solid

Safety Information

Hazard Codes 

Xi

Hazard Note 

Irritant

HS Code 

2916399090

tert-Butyl 4-bromo-2-nitrobenzoate Usage And Synthesis

Uses

4-Bromo-2-nitrobenzoate tert-butyl ester can be used as a pharmaceutical synthesis intermediate. It can be prepared by reacting 4-bromo-2-nitrobenzoic acid with 2-bromo-2-methylpropane. It can be used to prepare the compound 2-amino-4-bromobenzoate tert-butyl ester, which can also be widely used as a pharmaceutical synthesis intermediate.

Synthesis

To a solution containing 5.0 g of 4-bromo-2-nitrobenzoic acid 50 mL of N,N-dimethylacetamide was added 41 g of potassium carbonate, 4.6 g of benzyltriethylammonium chloride, and 69 mL of 2-bromo-2-methylpropane and stirred at 55 ??C for 10 hours. After the reaction mixture was cooled to room temperature, 12 mL of 2-bromo-2-methylpropane was added and stirred at 55??C for 4 hours. After cooling the reaction mixture to room temperature, water and ethyl acetate were added. The organic layer was separated and washed with 10% aqueous citric acid and saturated aqueous sodium chloride in turn, then dried with anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. Methanol was added to the obtained residue and 3.0 g of tert-butyl 4-bromo-2-nitrobenzoate was obtained as a white solid by filtration and separation of solids.1H-NMR (CDCl3) ??: 1.55 (9H, s), 7.63 (1H, d, J = 8.3 Hz), 7.77 (1H, dd, J = 8.3, 1.9 Hz), 7.95 (1H, d , J = 1.9 Hz).

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