Triphenylphosphine → {[2-(Methoxycarbonyl)phenyl]methyl}(triphenyl)phosphanium bromide

HRID 1885799Notes

Reaction equation

HRID 1885799 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Br:12]N1C(=O)CCC1=O.[C:20]1([P:26]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C(Cl)(Cl)Cl.C1(C)C=CC=CC=1>[Br-:12].[CH3:7][O:6][C:4]([C:3]1[CH:8]=[CH:9][CH:10]=[CH:11][C:2]=1[CH2:1][P+:26]([C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)=[O:5]

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 33094Methyl o-toluateHCID 67184N-bromobutanimide

Product 1

HCID 10743695{[2-(Methoxycarbonyl)phenyl]methyl}(triphenyl)phosphanium bromide

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6212ChloroformSolvent

Procedure

Methyl 2-methylbenzoate was treated successively with N-bromosuccinimide in chloroform and triphenylphosphine in toluene to give (o-methoxycarbonylbenzyl)triphenylphosphonium bromide as a white solid, mp. 230°-234° C., 1H NMR (D6 -DMSO) delta 3.36 (3H,s); 5.47 (2H, br d J 17 Hz) ppm.

Sources & evidence

ORD record
ord-742ba7f5c9ef4e209c7da9906d644a16
Source dataset
uspto-grants-1992_09
Patent number
US05145954

Reaction notes

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