Reaction #2139231

Reaction equation

2-(4-bromophenyl)-2-methyl-5-hydroxy-6,7-dichloro-1-indanone

potassium carbonate

ethyl bromoacetate

hydrochloric acid

sodium hydroxide

→

[1-Oxo-2-(4-bromophenyl)-2-methyl-6,7-dichloro-5-indanyloxy]acetic acid

Solvents

dimethylformamide

water

Conditions

Workup

1. 1
   Temperatureis warmed at 55°-60° C. for 3 hours
2. 2
   workup.ADDITIONThe reaction mixture is added slowly
3. 3
   Otherto precipitate 3.24 g
4. 4
   Otherof [1-oxo-2-(4-bromophenyl)-2-methyl-6,7-dichloro-5-indanyloxy]acetic acid which melts at 171°-172° C. after recrystallization from nitromethane

Procedure

A stirred mixture of 2-(4-bromophenyl)-2-methyl-5-hydroxy-6,7-dichloro-1-indanone (4.48 g., 0.0116 mole), potassium carbonate (3.88 g., 0.0232 mole) and ethyl bromoacetate (3.21 g., 0.0232 mole) in dimethylformamide (100 ml.) is warmed at 55°-60° C. for 3 hours, then treated with water (100 ml.)-10 N sodium hydroxide solution (5 ml., 0.05 mole) and heated at 100° C. for 2 hours. The reaction mixture is added slowly to crushed ice-water (1500 ml.)-12 N hydrochloric acid (50 ml.) to precipitate 3.24 g. of [1-oxo-2-(4-bromophenyl)-2-methyl-6,7-dichloro-5-indanyloxy]acetic acid which melts at 171°-172° C. after recrystallization from nitromethane followed by acetic acid:water, 3:2.

Source