Reaction #1772021

Reaction equation

EDCI

α-bromophenylacetic acid

(S)-(−)-1-phenylethanol

→

title compound

Yield 73.0%

(S)-1-Phenylethyl 2-bromo-2-phenylacetate

Yield 73.0%

Solvents

ethyl acetate

dichloromethane

Conditions

Workup

1. 1
   Washwashed (H2O×2, brine)
2. 2
   Dryingdried (Na2SO4)
3. 3
   Filtrationfiltered
4. 4
   Concentrationconcentrated
5. 5
   Otherto give a pale yellow oil

Procedure

To a mixture of α-bromophenylacetic acid (10.75 g, 0.050 mol), (S)-(−)-1-phenylethanol (7.94 g, 0.065 mol) and DMAP (0.61 g, 5.0 mmol) in dry dichloromethane (100 mL) was added solid EDCI (12.46 g, 0.065 mol) all at once. The resulting solution was stirred at room temperature under Ar for 18 hours and then it was diluted with ethyl acetate, washed (H2O×2, brine), dried (Na2SO4), filtered, and concentrated to give a pale yellow oil. Flash chromatography (SiO2/hexane-ethyl acetate, 4:1) of this oil provided the title compound (11.64 g, 73%) as a white solid. 1H NMR (400 MHz, CDCl3) δ 7.53-7.17 (m, 10H), 5.95 (q, J=6.6 Hz, 0.5H), 5.94 (q, J=6.6 Hz, 0.5H), 5.41 (s, 0.5H), 5.39 (s, 0.5H), 1.58 (d, J=6.6 Hz, 1.5H), 1.51 (d, J=6.6 Hz, 1.5H).

Source