Bromide ion → (2,6-Dichloro-3-methoxybenzyl)(triphenyl)phosphonium bromide

HRID 11072

Reaction equation

HRID 11072 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[C:4]([Cl:10])[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[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[C:4]([Cl:10])[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 21980844(2,6-Dichloro-3-methoxyphenyl)methanol

Product 1

HCID 87899066(2,6-Dichloro-3-methoxybenzyl)(triphenyl)phosphonium bromideYield 97%

Reagents, catalysts & solvents 2

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

Procedure

Bromination of (2,6-dichloro-3-methoxyphenyl)methanol with 30% HBr in acetic acid, followed by reaction of the crude bromide with triphenylphosphine, using the procedure described in example 112, except that the reaction time for the displacement was 36 h, gave the phosphonium salt (526) (97%) as a white solid, mp (CH2Cl2/benzene) 242–244° C. 1H NMR (CDCl3) δ 7.83–7.60 (m, 15H), 7.15 (dd, J=9.1, 0.8 Hz, 1H), 6.88 (dd, J=9.0, 2.4 Hz, 1H), 5.41 (d, J=14.3 Hz, 2H), 3.84 (s, 3H). Found: C, 58.68; H, 4.16. C26H22BrCl2OP requires C, 58.67; H, 4.17.

Sources & evidence

ORD record
ord-45cd2ce8b12c4a538ef3a33a64d2aec4
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Linked notes

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