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

HRID 11083

Reaction equation

HRID 11083 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH2:11]O.[BrH:13].[Br-].[C:15]1([P:21]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C(O)(=O)C.C(Cl)Cl.C1C=CC=CC=1>[Br-:13].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[CH2:11][P+:21]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 259Bromide ionHCID 260Hydrogen BromideHCID 11776TriphenylphosphineHCID 5557222-Chloro-5-nitrobenzyl alcohol

Product 1

HCID 11844221(2-Chloro-5-nitrobenzyl)(triphenyl)phosphonium bromideYield 63%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 23443464Methane, dichloro-, compd. with benzene (1:1)Solvent

Procedure

Bromination of (2-chloro-5-nitrophenyl)methanol with 30% HBr in acetic acid, followed by reaction of the crude bromide with triphenylphosphine, using the procedure described in example 112, gave the phosphonium salt (564) (63%) as a white solid, mp (CH2Cl2/benzene) 239–243° C. 1H NMR (CDCl3) δ 8.22 (br s, 1H), 8.07 (br d, J=8.7 Hz, 1H), 7.87–7.65 (m, 15H), 7.41 (d, J=8.9 Hz, 1H), 5.80 (d, J=14.8 Hz, 2H). Found: C, 58.56; H, 3.93; N, 2.73. C25H20BrClNO2P requires C, 58.47; H, 3.98; N, 2.66.

Sources & evidence

ORD record
ord-5ff65fcfe3074652ab6aafbfe9be302d
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Linked notes

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