2'-Bromoacetophenone → 1-Bromo-2-(prop-1-en-2-yl)benzene

HRID 339636

Reaction equation

HRID 339636 reaction equation
[CH3:1]C([O-])(C)C.[K+].[Br:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14](=O)[CH3:15]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[Br:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]([CH3:15])=[CH2:1]

Participants

5

Reactant 2

HCID 750602'-BromoacetophenoneHCID 23665647Potassium tert-butoxide

Product 1

HCID 124866181-Bromo-2-(prop-1-en-2-yl)benzeneYield 88%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of methyltriphenyl phosphonium bromide (108 g, 303 mmol) in THF (750 mL) at room temperature was added KOtBu (112.24 g, 303 mmol) in portions. After being stirred for 5 min, the reaction mixture was treated with 2′bromoacetophenone (50.3 g, 253 mmol). The reaction mixture was stirred for 3 hrs at room temperature then quenched with saturated ammonium chloride. Extracted 3× with Et2O and the combined organic layers were washed with brine, dried over MgSO4 and evaporated under vacuum. Purified by silica gel chromatography (100% petroleum ether) to give 43.8 g (88%) of 1-bromo-2-(prop-1-en-2-yl)benzene as a colorless oil.

Workup

  1. stirringThe reaction mixture was stirred for 3 hrs at room temperature
  2. customthen quenched with saturated ammonium chloride
  3. extractionExtracted 3× with Et2O
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. customevaporated under vacuum
  7. customPurified by silica gel chromatography (100% petroleum ether)

Sources & evidence

ORD record
ord-aca79341b3294c7c989a73bcd4f9138b
Source dataset
uspto-grants-2014_11
Patent number
US08895534B2

Linked notes

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