Ammonium Chloride → 1-(4-Ethyl-4-penten-1-yl)-2-iodobenzene

HRID 600745Notes

Reaction equation

[CH2:1]([Li])[CH2:2][CH2:3][CH3:4].[I:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH2:13][CH2:14][CH2:15]C(=O)CC.[Cl-].[NH4+]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCOCC>[CH2:2]([C:3](=[CH2:4])[CH2:15][CH2:14][CH2:13][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[I:6])[CH3:1]

Participants

Conditions

Temperature: 0 °C

Procedure

A suspension of methyltriphenylphosphonium bromide (21.76 g, 61 mmol) in dry ether (300 ml) was stirred at 0° C. under nitrogen. To this was added a 1.6M solution of butyl lithium (33.3 ml, 53.3 mmole) dropwise. Stirring at 0° C. was continued for 45 min then a solution of 6-(2-iodophenyl)-3-hexanone (Intermediate 10) (11.5 g, 38 mmol) in dry ether (40 ml) was added dropwise. Stirring at 0° C. was continued for 3 hours after which time aqueous ammonium chloride solution was added and the mixture was extracted with ether. The combined extracts were washed once with a mixture of ammonium chloride and sodium chloride solutions, dried over anhydrous magnesium sulphate and evaporated in vacuo. The residue was slurried with cyclohexane to extract the crude product. Purification by SPE eluting with cyclohexane gave the title compound as a colourless liquid (6.8 g, 60%).

Workup

stirringStirring at 0° C.
stirringStirring at 0° C.
waitwas continued for 3 hours
extractionthe mixture was extracted with ether
washThe combined extracts were washed once with a mixture of ammonium chloride and sodium chloride solutions
dry with materialdried over anhydrous magnesium sulphate
customevaporated in vacuo
extractionto extract the crude product
customPurification by SPE
washeluting with cyclohexane

Sources & evidence

ORD record: ord-0a4dcf269c9847688354bf6dea376217
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902224B2

Reaction notes

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