Triphenylphosphine → 2-Methoxycarbonylthiophen-3-ylmethyltriphenylphosphonium bromide

HRID 1831Notes

Reaction equation

HRID 1831 reaction equation
[Br:1][CH2:2][C:3]1[CH:7]=[CH:6][S:5][C:4]=1[C:8]([O:10][CH3:11])=[O:9].[C:12]1([P:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1(C)C=CC=CC=1>[Br-:1].[CH3:11][O:10][C:8]([C:4]1[S:5][CH:6]=[CH:7][C:3]=1[CH2:2][P+:18]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:9]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 10537693Methyl 3-(bromomethyl)thiophene-2-carboxylate

Product 1

HCID 196930522-Methoxycarbonylthiophen-3-ylmethyltriphenylphosphonium bromideYield 70.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of methyl 3-bromomethyl-2-thiophenecarboxylate (7.31 g, 31.1 mmol) in toluene (90 ml) was added triphenylphosphine (7.92 g, 30.2 mmol) under ice cooling. The temperature of the mixture was raised to room temperature, followed by stirring for 2 days. The precipitated crystals were collected by filtration and dried to give 2-methoxycarbonylthiophen-3-ylmethyltriphenylphosphonium bromide (10.57 g, 70.4%). This product was subjected to the reaction of Reference Example 13 without purification.

Workup

  1. filtrationThe precipitated crystals were collected by filtration
  2. customdried

Sources & evidence

ORD record
ord-f5ea82e1d125454e8bce94b7fc33917f
Source dataset
uspto-grants-1998_03
Patent number
US05726325

Reaction notes

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