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

HRID 405692

反応式

HRID 405692 の反応式
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]

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 1140Toluene溶媒HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-378b5957ca814ec68c328221864c4604
出典データセット
uspto-grants-2014_06
特許番号
US08754053B2

関連ノート

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