Reaction #302846

Reaction equation

hydrochloric acid

5′-bromo-2′-hydroxyacetophenone

compound 1

5′-bromo-2′-hydroxyacetophenone

4-nitrobenzoyl chloride

→

compound 2

4-nitrobenzoic acid 2-acetyl-4-bromophenyl ester

Solvents

pyridine

Conditions

Workup

1. 1
   OtherThe obtained mixture was reacted at room temperature for 30 minutes
2. 2
   Temperatureunder cooling on ice
3. 3
   FiltrationThe obtained precipitate was collected by filtration
4. 4
   Washthe filtrate was then washed with purified water

Procedure

5′-bromo-2′-hydroxyacetophenone (compound 1) (863 mg, 4.65 mmol) was added to a pyridine solution (20 ml) that contained 4-nitrobenzoyl chloride (1.00 g, 4.65 mmol) in an ice bath. The obtained mixture was reacted at room temperature for 30 minutes, and the reaction solution was then poured into 1 N hydrochloric acid under cooling on ice. The obtained mixture was intensively stirred. The obtained precipitate was collected by filtration, and the filtrate was then washed with purified water, so as to obtain a product of interest, 4-nitrobenzoic acid 2-acetyl-4-bromophenyl ester (compound 2). Yield: 1.57 g (yield constant: 92.7%) 1H NMR (300 MHz, CDCl3) δ 8.37 (s, 4H), 8.00 (s, 1H), 7.76-7.72 (m, 1H), 7.16 (d, J=8.7 Hz, 1H), 2.55 (s, 3H). MS m/z 365 (MH+).

Source