Carbon tetrabromide → HCID 86628049, compound

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][O:11][CH2:12][CH2:13]O)=[CH:5][CH:4]=1)#[N:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:35]>C(Cl)Cl>[Br:35][CH2:13][CH2:12][O:11][CH2:10][CH2:9][C:6]1[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=1

Participants

Procedure

To a solution of 2-[2-(4-cyanophenyl)ethoxy]ethanol (4.3 g, 0.0225 mol; see step (iv) above) in DCM (50 mL), triphenylphosphine (11.8 g, 0.045 mol) was added. The resulting mixture was stirred for 15 min and cooled to between 0 and 5° C. A solution of CBr4 (14.9 g, 0.045 mol) in DCM (25 mL) was added dropwise and the resulting mixture was stirred at room temperature overnight. The reaction mixture was concentrated and the crude product was purified by column chromatography (silica gel: 60-120 mesh, petroleum ether: ethyl acetate (70:30) eluent) to provide the title compound (yield: 4.8 g, 84%).