Reaction #1927

Reaction equation

methyl 3-bromomethyl-2-thiophenecarboxylate

triphenylphosphine

→

2-methoxycarbonylthiophen-3-ylmethyltriphenylphosphonium bromide

Yield 70.4%

Solvents

toluene

Conditions

Workup

1. 1
   FiltrationThe precipitated crystals were collected by filtration
2. 2
   Otherdried

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.

Source