Reaction #44170

Reaction equation

borane

(3-iodophenyl)acetic acid

ammonium chloride

→

title compound

Yield 92.4%

2-(3-Iodophenyl)ethanol

Yield 92.4%

Solvents

THF

Conditions

Workup

1. 1
   Temperaturecooled to 0 C
2. 2
   workup.STIRRINGstirred for a further 3 h
3. 3
   Extractionextracted with ethyl acetate
4. 4
   WashThe combined organic phases were washed with brine
5. 5
   Dryingdried (sodium sulfate)
6. 6
   Concentrationconcentrated
7. 7
   OtherThe crude was purified by column chromatography (SPE cartridge, SiO2)

Procedure

A solution of borane (1M, THF, 2.5 eq., 38.2 mL) was added dropwise to a stirred solution of (3-iodophenyl)acetic acid (4.0 g) in THF (100 mL) cooled to 0 C. The resulting mixture was stirred at 0 C for 1 h then warmed to room temperature and stirred for a further 3 h. The mixture was poured into aqueous ammonium chloride solution and extracted with ethyl acetate. The combined organic phases were washed with brine, dried (sodium sulfate) and concentrated. The crude was purified by column chromatography (SPE cartridge, SiO2), using cyclohexane-ethyl acetate (70:30) as eluent to afford the title compound (3.5 g, 92% yield).

Source