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

HRID 1393354

反応式

HRID 1393354 の反応式
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]

参加物

5

反応物 3

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

生成物 1

HCID 230339255-Chloro-2-trifluoromethanesulfonyloxy-3-nitrobenzoic acid収率 95.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-6c43c697bb934391954883510eedae39
出典データセット
uspto-grants-2008_03
特許番号
US07345068B2

関連ノート

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