Triphenylphosphine → 2-Chloro-4-(methylsulfanyl)benzaldehyde

HRID 2380207ノート

反応式

HRID 2380207 の反応式
[Cl:1][C:2]1[CH:10]=[C:9]([S:11][CH3:12])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CC(C)=O.[B-].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu+]>[Cl:1][C:2]1[CH:10]=[C:9]([S:11][CH3:12])[CH:8]=[CH:7][C:3]=1[CH:4]=[O:5]

参加物

5

反応物 2

HCID 11776TriphenylphosphineHCID 189779562-Chloro-4-methylsulphenylbenzoyl chloride

生成物 1

HCID 199317902-Chloro-4-(methylsulfanyl)benzaldehyde収率 98.3%

試薬・触媒・溶媒 2

HCID 10908163Bis (triphenylphosphine) copper (I) borohydride触媒2 回HCID 180Acetone溶媒

反応条件

温度
0 °C

実験手順

A mixture of 2-chloro-4-(methylsulphenyl)-benzoyl chloride (1.0 g), triphenyl phosphine (2.47 g) and bis(triphenylphosphine)copper (I) borohydride (1.0 g) in acetone was stirred at 0° C. for 1 hour. Further bis (triphenylphosphine)copper (I) borohydride (1.5 g) was added and the mixture was stirred for 2 hours. The mixture was filtered and the filtrate was evaporated to dryness. The residue was dissolved in chloroform and treated with copper (I) bromide (2.1 g). The filtrate was evaporated to dryness and the residue was purified by chromotography eluted with a mixture of ethyl acetate and hexane to give 2-chloro-4-(methylsulphenyl)benzaldehyde (0.83 g) as an off-white solid, m.p. 76°-77° C.

後処理

  1. stirringthe mixture was stirred for 2 hours
  2. filtrationThe mixture was filtered
  3. customthe filtrate was evaporated to dryness
  4. dissolutionThe residue was dissolved in chloroform
  5. additiontreated with copper (I) bromide (2.1 g)
  6. customThe filtrate was evaporated to dryness
  7. customthe residue was purified by chromotography
  8. washeluted with a mixture of ethyl acetate and hexane

出典と根拠

ORDレコード
ord-de0b613f9c7a4e388cb4e332f62074ae
出典データセット
uspto-grants-1994_11
特許番号
US05366957

反応ノート

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