Triphenylphosphine → (3-Methylbut-2-enyl)triphenylphosphonium bromide

HRID 2052371

Reaction equation

HRID 2052371 reaction equation
[CH3:1][C:2]([CH3:6])=[CH:3][CH2:4][Br:5].[C:7]1([P:13]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C1(C)C=CC=CC=1>[Br-:5].[CH3:1][C:2]([CH3:6])=[CH:3][CH2:4][P+:13]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 700922-Butene, 1-bromo-3-methyl-

Product 1

HCID 3083722(3-Methylbut-2-enyl)triphenylphosphonium bromide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 3,3-dimethylallyl bromide (50.0 g), triphenylphosphine (88.0 g) and dry toluene (500 ml) was stirred and heated at the reflux temperature for one hour, and then kept at the ambient temperature for 18 hours. The white precipitate of 3,3-dimethylallyl triphenylphosphonium bromide (m.p. 242° C.) was collected by filtration, washed with diethyl ether and dried.

Workup

  1. temperatureheated at the reflux temperature for one hour
  2. filtrationThe white precipitate of 3,3-dimethylallyl triphenylphosphonium bromide (m.p. 242° C.) was collected by filtration
  3. washwashed with diethyl ether
  4. customdried

Sources & evidence

ORD record
ord-78114930e25046a38384aa52a8fa728f
Source dataset
uspto-grants-1980_01
Patent number
US04183948

Linked notes

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