Hydrochloric Acid → Methyl 3-chloro-4-fluoro-alpha-azidocinnamate

HRID 2396851노트

반응식

HRID 2396851 반응식
[Na].[Cl:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[F:11])[CH:6]=O.[N:12]([CH2:15][C:16]([O:18][CH3:19])=[O:17])=[N+:13]=[N-:14].Cl>CO>[Cl:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[F:11])[CH:6]=[C:15]([N:12]=[N+:13]=[N-:14])[C:16]([O:18][CH3:19])=[O:17]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 5938663-Chloro-4-fluorobenzaldehydeHCID 4020482Methyl 2-azidoacetateHCID 5360545Sodium

생성물 1

HCID 54554773Methyl 3-chloro-4-fluoro-alpha-azidocinnamate수율 33.3%

시약·촉매·용매 1

HCID 887Methanol용매2회

실험 절차

While cooling with an ice bath 1.35 g of sodium were dissolved in 30 ml of methanol and subsequently a solution of 4.65 g of 3-chloro-4-fluorobenzaldehyde and 6.75 g of methyl azidoacetate in 10 ml of methanol were added within 20 min. The reaction mixture was stirred at room temperature for 3 hours and then neutralized with 2N HCl. The mixture was extracted with ethyl acetate, washed with water and saturated sodium chloride solution and the organic phase was dried over sodium sulfate. The solvent was removed and the residue was chromatographed over 250 g of silica gel with n-hexane-toluene 2:1. There were obtained 2.5 g (33%) of methyl 3-chloro-4-fluoro-a-azidocinnamate as yellow crystals with m.p. 72°-74°.

후처리

  1. extractionThe mixture was extracted with ethyl acetate
  2. washwashed with water and saturated sodium chloride solution
  3. dry with materialthe organic phase was dried over sodium sulfate
  4. customThe solvent was removed
  5. customthe residue was chromatographed over 250 g of silica gel with n-hexane-toluene 2:1

출처 및 근거

ORD 기록
ord-bf961dd54b9a4058ae58ca485f5c2e7d
출처 데이터셋
uspto-grants-1996_02
특허 번호
US05494928

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