Triphenylphosphine → 3-(5-Bromopentyl)-5-methylisoxazole

Reaction equation

O[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[CH:11]=[C:10]([CH3:12])[O:9][N:8]=1.BrBr.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC1ON=C(CCC[Br:43])C=1>>[Br:43][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]1[CH:11]=[C:10]([CH3:12])[O:9][N:8]=1

Participants

Reactant 4

HCID 11776Triphenylphosphine

HCID 24408Bromine

HCID 133169753-(3-Bromopropyl)-5-methyl-1,2-oxazole

HCID 133169773-(5-Hydroxypentyl)-5-methylisoxazole

Product 1

HCID 133169783-(5-Bromopentyl)-5-methylisoxazoleYield 77%

Procedure

3-(5-Bromopentyl)-5-methylisoxazole [XXVII; R9 =CH3, Hal=Br] was prepared by reacting 3-(5-hydroxypentyl)-5-methylisoxazole with bromine and triphenylphosphine according to the procedure of part (f) above, and was obtained in 77% yield as an oil, b.p. 140°-150° C.(0.05 mm).