Triphenylphosphine → HCID 21390533, compound

HRID 462096Notes

Reaction equation

HRID 462096 reaction equation
[Br:1][CH2:2][C:3]1[S:7][C:6]([C:8]([OH:10])=[O:9])=[CH:5][CH:4]=1.[C:11]1([P:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(#N)C>[Br-:1].[C:8]([C:6]1[S:7][C:3]([CH2:2][P+:17]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[CH:4][CH:5]=1)([OH:10])=[O:9]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 158875035-(Bromomethyl)thiophene-2-carboxylic acid

Product 1

HCID 21390533HCID 21390533, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2.54 g. (11.5 mmoles) of 5-bromomethylthiophene-2-carboxylic acid and 3.02 g. of triphenylphosphine in 50 ml. of acetonitrile was heated at reflux for 1.5 hours then was cooled. The resultant precipitate was collected by filtration and was recrystallized from ethanol:hexane to provide the (2-carboxythiophen-5-yl-methyl)triphenylphosphonium bromide weighing 3.16 g. and melting at 273°.

Workup

  1. additionA mixture of 2.54 g
  2. temperatureat reflux for 1.5 hours
  3. temperaturethen was cooled
  4. filtrationThe resultant precipitate was collected by filtration
  5. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-466454f0cf4e47aeb697c2181ec04b15
Source dataset
uspto-grants-1977_12
Patent number
US04065472

Reaction notes

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