Toluene → Phosphonium, (4-methylpentyl)triphenyl-, bromide

HRID 2103595Notes

Reaction equation

[Br:1]CCC(C)(C)C.[C:8]1([P:14]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[C:27]1([CH3:33])[CH:32]=C[CH:30]=[CH:29][CH:28]=1>>[Br-:1].[CH3:32][CH:27]([CH3:33])[CH2:28][CH2:29][CH2:30][P+:14]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

Reactant 3

HCID 1140Toluene

HCID 11776Triphenylphosphine

HCID 1371371-Bromo-3,3-dimethylbutane

Product 1

HCID 10928070Phosphonium, (4-methylpentyl)triphenyl-, bromide

Conditions

Temperature: 190 °C

Procedure

Dissolve 1-bromo-3,3-dimethylbutane(9.6 g, 58.15 mmol) in toluene, add triphenyl-phosphine (13.8 g, 55.2 mmol) and stir at 80° C. for 4 days in a scewcapglass and 3 days in an autoklav at 4 bar and 190° C. Cool the reaction mixture down to room temperature and isolate the product by crystallization in ether as a white solid (9.8 g). MS (m/e): 347 (M+H).

Workup

temperatureCool the reaction mixture down to room temperature
customisolate the product
customby crystallization in ether as a white solid (9.8 g)

Sources & evidence

ORD record: ord-972bc30b37ff4370af345ec0e1c9b017
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576108B2

Reaction notes

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