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

HRID 1073689

Reaction equation

HRID 1073689 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-dimethylall-yl 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-dimethylall-yl triphenylphosphonium bromide (m.p. 242° C.) was collected by filtration
  3. washwashed with diethyl ether
  4. customdried

Sources & evidence

ORD record
ord-3f4384b5fe984591a934eb49c1c3c893
Source dataset
uspto-grants-1990_11
Patent number
US04970330

Linked notes

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