Carbon tetrabromide → 4-(3-Bromo-propyl)-5-methyl-2-phenyl-oxazole

Participants

Reaction Conditions

Reaction Steps

Alcohol 1-4 (3 g, 13.8 mmol) was dissolved in dichloromethane (200 mL) and cooled to 0° C. under N2 atmosphere. Triphenylphosphine (4.35 g, 16.6 mmol) was added followed by CBr4 (5.5 g, 16.6 mol) in small portions. Reaction temperature was allowed to equilibrate to 23° C. over 8 hours. 20 g of SiO2 gel was added and solvent removed in vacuo. The dried silica gel was placed in a filter and washed with 10% EtOAc/Hexanes. The filtrate was reduced to minimum volume and chromatographed with 5-10% EtOAc/Hexanes to give 3.5 g of the product 1-5 as a clear oil (90% yield). M+1=280.0/282.1.

Provenance & Evidence