Acetic Acid → 3-Chloro-4,5-difluoroanthranilic acid

HRID 10317

反応式

HRID 10317 の反応式
[F:1][C:2]1[CH:3]=[C:4]([NH2:12])[C:5](=[CH:9][C:10]=1[F:11])[C:6]([OH:8])=[O:7].C(O)(=O)C.C(O[Cl:22])(C)(C)C>ClCCl.C(OCC)(=O)C>[Cl:22][C:3]1[C:2]([F:1])=[C:10]([F:11])[CH:9]=[C:5]([C:6]([OH:8])=[O:7])[C:4]=1[NH2:12]

参加物

6

反応物 3

HCID 176Acetic AcidHCID 521297Tert-Butyl hypochloriteHCID 7359652-Amino-4,5-difluorobenzoic acid

生成物 1

HCID 219789243-Chloro-4,5-difluoroanthranilic acid収率 100.8%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 4,5-difluoroanthranilic acid (2.45 g, 14.2 mmol) in dichloromethane (25 mL) is added acetic acid (10 mL) and hypochlorous acid tert-butyl ester (1.75 mL, 15.6 mmol). After 2 hours, the reaction mixture is diluted with ethyl acetate and washed with water and brine. The organic layer is dried over MgSO4, filtered, and concentrated. The resulting residue is purified via flash column chromatography (5% isopropyl alcohol/1% formic acid/94% dichloromethane) to afford 3-chloro-4,5-difluoroanthranilic acid as an oil (2.97 g). MS CI: m/z 206 (M+).

後処理

  1. washwashed with water and brine
  2. dry with materialThe organic layer is dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting residue is purified via flash column chromatography (5% isopropyl alcohol/1% formic acid/94% dichloromethane)

出典と根拠

ORDレコード
ord-cce603932cca4abba7de902112a6eb98
出典データセット
uspto-grants-2006_08
特許番号
US07094780B1

関連ノート

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