Diethyl Ether → (3,4-Dimethoxybenzyl)triphenylphosphonium Bromide

HRID 1110798Notes

Reaction equation

HRID 1110798 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][Br:12])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[C:13]1([P:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(OCC)C>CN(C)C=O>[Br-:12].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][P+:19]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 11776TriphenylphosphineHCID 109004583,4-Dimethoxybenzyl bromide

Product 1

HCID 11049284(3,4-Dimethoxybenzyl)triphenylphosphonium BromideYield 80.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3,4-Dimethoxy-α-bromotoluene (11.6 g) [Gordon N. Walker et al., J. Org. Chem., 26, 2740 (1961)] and triphenylphosphine (13.11 g) are heated in dimethylformamide (150 cc) at 75° C. for 1 hour 30 minutes. After addition of ethyl ether (700 cc) to the reaction mixture and filtration, 3,4-dimethoxyphenylmethyltriphenylphosphonium bromide (19.8 g) is obtained in the form of a white solid melting at 260° C.

Workup

  1. filtrationto the reaction mixture and filtration

Sources & evidence

ORD record
ord-d9303906a21e41618d7a0c92d2070c4e
Source dataset
uspto-grants-1990_12
Patent number
US04977166

Reaction notes

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