Triphenylphosphine → 1-(4-Bromo-3-methyl-phenyl)-2-(triphenylphosphanylidene)-ethanone

HRID 405692

Reaction equation

HRID 405692 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[C:7]([CH3:12])[CH:6]=1)=[O:4].[C:13]1([P:19]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)(O)[O-].[Na+]>ClCCl.C1(C)C=CC=CC=1.O>[Br:11][C:8]1[CH:9]=[CH:10][C:5]([C:3](=[O:4])[CH:2]=[P:19]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)=[CH:6][C:7]=1[CH3:12]

Participants

7

Reactant 3

HCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 591663462-Bromo-1-(4-bromo-3-methylphenyl)ethanone

Product 1

HCID 866746711-(4-Bromo-3-methyl-phenyl)-2-(triphenylphosphanylidene)-ethanone

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

1300 mg of 2-Bromo-1-(4-bromo-3-methyl-phenyl)-ethanone (VIIa) (Journal of Organic Chemistry (1947), 12, 617-703) was stirred with 1300 mg of triphenylphosphine in 20 ml of dichloromethane at ambient temperature for 18 hours. The mixture was diluted with toluene and the separated phosphonium salt was filtered off. It was then suspended in 20 ml of dichloromethane and 20 ml of water. 800 mg (7.55 mmol) of sodium bicarbonate was then added in 20 ml of water and the mixture was stirred overnight. The organic layer was separated, dried and evaporated under reduced pressure. The residue was triturated with hexane giving 1.6 g (86%) of 1-(4-Bromo-3-methyl-phenyl)-2-(triphenylphosphanylidene)-ethanone (Va) as a solid. 1H-NMR (CDCl3, δ in ppm): 7.40-7.90 (m, 18H), 4.40 (m, 1H).

Workup

  1. filtrationthe separated phosphonium salt was filtered off
  2. customThe organic layer was separated
  3. customdried
  4. customevaporated under reduced pressure
  5. customThe residue was triturated with hexane giving 1.6 g (86%) of 1-(4-Bromo-3-methyl-phenyl)-2-(triphenylphosphanylidene)-ethanone (Va) as a solid

Sources & evidence

ORD record
ord-378b5957ca814ec68c328221864c4604
Source dataset
uspto-grants-2014_06
Patent number
US08754053B2

Linked notes

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