Reaction #302853

Reaction equation

hydrochloric acid

5′-bromo-2′-hydroxyacetophenone

compound 12

5′-bromo-2′-hydroxyacetophenone

4-methoxybenzoyl chloride

→

compound 13

4-methoxybenzoic 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 12) (1.80 g, 10.6 mmol) was added to a pyridine solution (40 ml) that contained 4-methoxybenzoyl chloride (2.01 g, 9.35 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-methoxybenzoic acid 2-acetyl-4-bromophenyl ester (compound 13). Yield: 3.15 g (yield constant: 96.5%) 1H NMR (300 MHz, CDCl3) δ 7.72 (d, J=7.5 Hz, 1H), 8.06 (d, J=7.2 Hz, 1H), 8.86 (s, 1H), 10.13 (s, 1H).

Source