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

HRID 2380207노트

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HRID 2380207 반응식
[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]

참가 물질

5

반응물 2

HCID 11776TriphenylphosphineHCID 189779562-Chloro-4-methylsulphenylbenzoyl chloride

생성물 1

HCID 199317902-Chloro-4-(methylsulfanyl)benzaldehyde수율 98.3%

시약·촉매·용매 2

HCID 10908163Bis (triphenylphosphine) copper (I) borohydride촉매2회HCID 180Acetone용매

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-de0b613f9c7a4e388cb4e332f62074ae
출처 데이터셋
uspto-grants-1994_11
특허 번호
US05366957

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