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

HRID 488509
Notes
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Reaction equation

HRID 488509 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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 222697304-(4-Nitrophenyl)butanalHCID 22269763Bromo[(3,4-dichlorophenyl)methyl]triphenylphosphorane

Product 1

HCID 540012121,2-Dichloro-4-[5-(4-nitrophenyl)-1-pentenyl]benzeneYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

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

  1. temperatureto warm to room temperature within 2 hours
  2. customThe mixture was then quenched with H2O
  3. extractionextracted with EtOAc
  4. washThe organic layers were washed with 0.1N HCl solution, H2O, brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a lightly brown oil
  9. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes