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

HRID 405692

반응식

HRID 405692 반응식
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]

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 962Water용매HCID 1140Toluene용매HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-378b5957ca814ec68c328221864c4604
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08754053B2

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