2,6-Lutidine → 5-Chloro-2-trifluoromethanesulfonyloxy-3-nitrobenzoic acid

HRID 1393354

반응식

HRID 1393354 반응식
N1C(C)=CC=CC=1C.[F:9][C:10]([F:23])([F:22])[S:11]([O:14]S(C(F)(F)F)(=O)=O)(=[O:13])=[O:12].[Cl:24][C:25]1[CH:33]=[C:29]([C:30]([OH:32])=[O:31])[C:28](O)=[C:27]([N+:35]([O-:37])=[O:36])[CH:26]=1>C(Cl)Cl>[Cl:24][C:25]1[CH:26]=[C:27]([N+:35]([O-:37])=[O:36])[C:28]([O:14][S:11]([C:10]([F:23])([F:22])[F:9])(=[O:13])=[O:12])=[C:29]([CH:33]=1)[C:30]([OH:32])=[O:31]

참가 물질

5

반응물 3

HCID 79372,6-LutidineHCID 67749Trifluoromethanesulfonic anhydrideHCID 4120785-Chloro-2-hydroxy-3-nitrobenzoic acid

생성물 1

HCID 230339255-Chloro-2-trifluoromethanesulfonyloxy-3-nitrobenzoic acid수율 95.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

2,6-Lutidine (1.83 ml, 15.7 mmol) and trifluoro-methanesulfonic anhydride (3.67 g, 13 mmol) were added dropwise in turn to a solution of methyl ester of 5-chloro-3-nitrosalicylic acid (2.32 g, 10.0 mmol) in methylene chloride (25 ml) with stirring under ice cooling and the mixture was stirred under ice cooling for 0.5 hrs. Methylene chloride (20 ml) and ice water (30 ml) were added to the reaction mixture and the aqueous layer was separated and extracted with methylene chloride. The organic layers were combined, washed with water and dried. The solvent was distilled off under reduced pressure and the residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=10) to give methyl ester of 5-chloro-2-trifluoromethanesulfonyloxy-3-nitrobenzoic acid (3.33 g, 91%) as a pale yellow oil.

후처리

  1. stirringthe mixture was stirred under ice cooling for 0.5 hrs
  2. customthe aqueous layer was separated
  3. extractionextracted with methylene chloride
  4. washwashed with water
  5. customdried
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate=10)

출처 및 근거

ORD 기록
ord-6c43c697bb934391954883510eedae39
출처 데이터셋
uspto-grants-2008_03
특허 번호
US07345068B2

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