Triphenylphosphine → (tert-Butoxycarbonylmethyl)triphenylphosphonium Bromide

HRID 2106870Notes

Reaction equation

HRID 2106870 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 vacuo 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 vacuo

Sources & evidence

ORD record
ord-f6b3f10780de4177b168c8ba64a75c9b
Source dataset
uspto-grants-1990_06
Patent number
US04931469

Reaction notes

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