Carbon tetrabromide → Methyl 4-(1-bromobutyl)benzoate

Reaction equation

C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O[CH:21]([C:25]1[CH:34]=[CH:33][C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:27][CH:26]=1)[CH2:22][CH2:23][CH3:24].C(Br)(Br)(Br)[Br:36]>C(Cl)Cl>[Br:36][CH:21]([C:25]1[CH:34]=[CH:33][C:28]([C:29]([O:31][CH3:32])=[O:30])=[CH:27][CH:26]=1)[CH2:22][CH2:23][CH3:24]

Participants

Procedure

A solution of PPh3 (42.2 g. 320 mmol) in DCM (200 mL) was added dropwise to a solution of methyl 4-(1-hydroxybutyl)benzoate (33.5 g, 160 mmol) and CBr4 (53.1 g, 320 mmol) in DCM (1200 mL) at 0° C. Once the addition was complete, the mixture was allowed to warm to room temperature and was stirred overnight. The mixture was concentrated, then the resulting residue was purified by silica gel chromatography eluting with 5% EtOAc/petroleum ether to afford the title compound. 1H NMR (300 MHz, CDCl3) δ 8.00 (d, J=6 Hz, 2 H); 7.45 (d, J=6 Hz, 2 H); 4.95 (t, J=7 Hz, 1 H); 3.91 (s, 3 H); 2.19-2.32 (m, 1 H); 2.02-2.14 (m, 1 H); 1.43-1.55 (m, 1 H); 1.24-1.38 (m, 1 H); 0.93 (t, J=7 Hz, 3 H).