Bromide ion → (2-Chloro-5-methoxybenzyl)(triphenyl)phosphonium bromide

HRID 11086

Reaction equation

HRID 11086 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH3:10].C1C(=O)N([Br:18])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C.[Br-].[C:32]1([P:38]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C(Cl)Cl.C1C=CC=CC=1>[Br-:18].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[CH2:10][P+:38]([C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

6

Reactant 4

HCID 259Bromide ionHCID 11776TriphenylphosphineHCID 4581561-Chloro-4-methoxy-2-methylbenzeneHCID 86630000Nbs aibn

Product 1

HCID 85758264(2-Chloro-5-methoxybenzyl)(triphenyl)phosphonium bromideYield 76%

Reagents, catalysts & solvents 1

HCID 23443464Methane, dichloro-, compd. with benzene (1:1)Solvent

Procedure

Bromination of 1-chloro-4-methoxy-2-methylbenzene with NBS/AIBN, followed by reaction of the crude bromide with triphenylphosphine, using the procedure described in example 102, except that the reaction time for the bromination was 4 h, gave the phosphonium salt (578) (76%) as a light brown solid, mp (CH2Cl2/benzene) 189–190.5° C. 1H NMR (CDCl3) δ 7.82–7.61 (m, 15H), 7.21 (t, J=2.8 Hz, 1H), 7.04 (dd, J=8.8, 0.8 Hz, 1H), 6.76 (dt, J=8.9, 2.7 Hz, 1H), 5.59 (d, J=14.4 Hz, 2H), 3.58 (s, 3H). Found: C, 62.75; H, 4.70. C26H23BrClOP requires-C, 62.73; H, 4.66.

Sources & evidence

ORD record
ord-bfdc92081d604501937dbab0c74fb0e9
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Linked notes

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