Réaction #44170

Équation de réaction

borane

(3-iodophenyl)acetic acid

ammonium chloride

→

title compound

Rendement 92.4%

2-(3-Iodophenyl)ethanol

Rendement 92.4%

Solvants

THF

Conditions de réaction

Traitement

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

Mode opératoire

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