Triphenylphosphine → (E)-2-(1-methoxy-2-methoxycarbonylethenyl)benzyltriphenylphosphonium bromide

HRID 1899783Notes

Reaction equation

HRID 1899783 reaction equation
[Br:1][CH2:2][C:3]1[CH:16]=[CH:15][CH:14]=[CH:13][C:4]=1/[C:5](/[O:11][CH3:12])=[CH:6]\[C:7]([O:9][CH3:10])=[O:8].[C:17]1([P:23]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>O1CCCC1>[Br-:1].[CH3:12][O:11]/[C:5](/[C:4]1[CH:13]=[CH:14][CH:15]=[CH:16][C:3]=1[CH2:2][P+:23]([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[CH:6]/[C:7]([O:9][CH3:10])=[O:8]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 11219857methyl (E)-2-bromomethyl-beta-methoxycinnamate

Product 1

HCID 23371326(E)-2-(1-methoxy-2-methoxycarbonylethenyl)benzyltriphenylphosphonium bromideYield 82.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

115 g (0.4 mol) of methyl (E)-2-bromomethyl-β-methoxycinnamate and 105 g (0.4 mol) of triphenylphosphine in 700 ml of tetrahydrofuran are refluxed for 24 h. Filtration with suction and washing with tetrahydrofuran result in 181 g (82% yield) of (E)-2-(1-methoxy-2-methoxycarbonylethenyl)benzyltriphenylphosphonium bromide in the form of colorless crystals with melting point 189-°192° C.

Workup

  1. filtrationFiltration with suction
  2. washwashing with tetrahydrofuran

Sources & evidence

ORD record
ord-80067e668ab04539b864004e5bf00d7b
Source dataset
uspto-grants-1996_11
Patent number
US05573999

Reaction notes

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