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

HRID 21460노트

반응식

HRID 21460 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) borohydride촉매HCID 180Acetone용매

반응 조건

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 his (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-2216a806563e452ca7db02216554b46a
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05424276

반응 노트

불러오는 중…