Reaction #4376

Reaction equation

3-methoxybenzeneacetic acid

iodine monochloride

water

→

2-iodo-5-methoxybenzeneacetic acid

Yield 65.0%

Solvents

acetic acid

Conditions

Workup

1. 1
   Otherthe solid collected
2. 2
   OtherIt was recrystallized from toluene

Procedure

A solution of 45 g (0.27 mole) of 3-methoxybenzeneacetic acid, 52.6 g (0.32 mole) of iodine monochloride and 1 g of iodine was allowed to stand in 500 ml of glacial acetic acid for six days at room temperature. The reaction was poured into water and the solid collected. It was recrystallized from toluene to give 51 g of crystalline 2-iodo-5-methoxybenzeneacetic acid, mp 133.5°-134.5° C. (65% yield).

Source