Ethanol → HCID 10590086, compound

Reaction equation

P(Br)(Br)[Br:2].[CH:5]([C:8]1[CH:15]=[C:14]([CH:16]([CH3:18])[CH3:17])[CH:13]=[C:12]([CH:19]([CH3:21])[CH3:20])[C:9]=1[CH2:10]O)([CH3:7])[CH3:6].C(O)C>C(OCC)C>[CH:5]([C:8]1[CH:15]=[C:14]([CH:16]([CH3:18])[CH3:17])[CH:13]=[C:12]([CH:19]([CH3:21])[CH3:20])[C:9]=1[CH2:10][Br:2])([CH3:7])[CH3:6]

Participants

Procedure

A solution of phosphorus tribromide (3.8 mL, 0.04 mol) in ethyl ether (150 mL) was added dropwise to 2,4,6-triisopropylbenzyl alcohol (17.99 g, 0.076 mol) in ethyl ether (350 mL) at room temperature under a nitrogen atmosphere. The reaction mixture was stirred overnight at room temperature. Ethanol (95%, 50 mL) was added dropwise over 1 hour and the resulting mixture was stirred for 30 minutes, and was then concentrated to an oil. The oil was partitioned between ethyl acetate (300 mL) and saturated aqueous sodium bicarbonate. The organic layer was washed with water (50 mL), dried (magnesium sulfate), filtered, and concentrated to a clear liquid (22.56 g, 98.9%). This was used directly in the next step.