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].CCO>CCOCC>[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 PBr3 (2.7 9, 10 mmol) in ether (10 mL) was added slowly to a solution of 2,4,6-triisopropylbenzyl alcohol (4.68 9, 20 mmol) in 20 mL of ether at room temperature. The mixture was stirred for 1 hour, 5 mL of absolute EtOH was added, and stirring was continued for another 0.5 hour. The solvent was removed and the residue distributed between EtOAc and saturated Na2CO3. The EtOAc layer was separated, washed with brine, and dried over MgSO4. The solvent was evaporated and the pure product was isolated by column chromatography (100% CH2Cl2, 3.5 g, 59%); NMR (CDCl3):δ 1.2-1.4 (m, 18H), 2.8-3.0 (m, 1H), 3.2-3.45 (m, 2H), 4.7 (s, 2H), 7.04 (s, 2H) ppm.