Sodium Thiosulfate → Methyl 5-bromo-4-cyclopropyl-2-isopropoxybenzoate

HRID 531026ノート

反応式

HRID 531026 の反応式
[Br:1]N1C(=O)NC(=O)N(Br)C1=O.[CH:12]1([C:15]2[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[C:17]([O:25][CH:26]([CH3:28])[CH3:27])[CH:16]=2)[CH2:14][CH2:13]1.S([O-])([O-])(=O)=S.[Na+].[Na+]>CN(C=O)C>[Br:1][C:24]1[C:15]([CH:12]2[CH2:14][CH2:13]2)=[CH:16][C:17]([O:25][CH:26]([CH3:28])[CH3:27])=[C:18]([CH:23]=1)[C:19]([O:21][CH3:22])=[O:20]

参加物

5

反応物 3

HCID 24477Sodium ThiosulfateHCID 192912Dibromoisocyanuric acidHCID 90423653Methyl 4-cyclopropyl-2-isopropoxybenzoate

生成物 1

HCID 90423660Methyl 5-bromo-4-cyclopropyl-2-isopropoxybenzoate収率 158.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

Dibromoisocyanuric acid (3.99 g) was added at room temperature to a DMF (80 mL) solution of methyl 4-cyclopropyl-2-isopropoxybenzoate (5.43 g), and the mixture was stirred at 90° C. for 1 hour in a nitrogen atmosphere. An aqueous sodium thiosulfate solution was added to the reaction mixture at room temperature, followed by extraction with ethyl acetate. The obtained organic layer was washed with water and saturated saline in this order and dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (6.89 g).

後処理

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe obtained organic layer was washed with water and saturated saline in this order
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-bb46b8ec3cdb4ed89c25df30a230dc26
出典データセット
uspto-grants-2016_05
特許番号
US09353108B2

反応ノート

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