4-(4-Nitrophenyl)butanal → 1,2-Dichloro-4-[5-(4-nitrophenyl)-1-pentenyl]benzene

HRID 488509Notes

Reaction equation

BrP([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([Cl:29])[CH:23]=1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[N+:30]([C:33]1[CH:38]=[CH:37][C:36]([CH2:39][CH2:40][CH2:41][CH:42]=O)=[CH:35][CH:34]=1)([O-:32])=[O:31]>C1COCC1>[Cl:28][C:25]1[CH:26]=[CH:27][C:22]([CH:21]=[CH:42][CH2:41][CH2:40][CH2:39][C:36]2[CH:37]=[CH:38][C:33]([N+:30]([O-:32])=[O:31])=[CH:34][CH:35]=2)=[CH:23][C:24]=1[Cl:29]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of bromo[(3,4-dichlorophenyl)methyl]triphenylphosphine (3.95 g, 7.9 mmol) in dry THF (20 mL) was cooled to 0° C. LHDMS (1.0 M/THF, 9 ml, 9.0 mol) was added dropwise to maintain the temperature at 0° C. After stirring for 30 minutes, a solution of 4-(4-nitro-phenyl)butyraldehyde (1.45 g, 7.5 mmol) in TBF (5 mL) was added dropwise, and the mixture was allowed to warm to room temperature within 2 hours. The mixture was then quenched with H2O and extracted with EtOAc. The organic layers were washed with 0.1N HCl solution, H2O, brine, dried (Na2SO4), filtered, and concentrated in vacuo to give a lightly brown oil. Purification by flash chromatography (silica gel, 10% EtOAc/hexane) yielded 2.5 g (7.4 mmol, 99%) of the desired product.

Workup

temperatureto warm to room temperature within 2 hours
customThe mixture was then quenched with H2O
extractionextracted with EtOAc
washThe organic layers were washed with 0.1N HCl solution, H2O, brine
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated in vacuo
customto give a lightly brown oil
customPurification by flash chromatography (silica gel, 10% EtOAc/hexane)

Sources & evidence

ORD record: ord-204456296c9d4f79958dc86a844ea959
Source dataset: uspto-grants-2005_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06972287B1

Reaction notes

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