Triphenylphosphine → (tert-Butoxycarbonylmethyl)triphenylphosphonium Bromide

HRID 1722232Notes

Reaction equation

HRID 1722232 reaction equation
[C:1]1([P:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:20][CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23]>C1C=CC=CC=1>[Br-:20].[C:22]([CH2:21][P+:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 79177tert-Butyl bromoacetate

Product 1

HCID 2733853(tert-Butoxycarbonylmethyl)triphenylphosphonium BromideYield 96%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of triphenylphosphine (33.8 g, 129 mmol) and t-butyl bromoacetate (25 g, 128.2 mmol) in dry benzene (150 ml) was stirred for 16 hours at room temperature. The precipitated product was collected by filtration, washed with dry ether and dried in vaco to give 56 g (96% of theory) of carbo-t-butoxymethyl triphenylphosphonium bromide.

Workup

  1. filtrationThe precipitated product was collected by filtration
  2. washwashed with dry ether
  3. customdried in vaco

Sources & evidence

ORD record
ord-b5d2fac81ff3499d9df07ea72bbc78c3
Source dataset
uspto-grants-1989_08
Patent number
US04855086

Reaction notes

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