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

HRID 2272474노트

반응식

HRID 2272474 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 90423660Methyl 5-bromo-4-cyclopropyl-2-isopropoxybenzoate수율 158.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-9f39acd764c64ecc883f955dc969ab87
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09120777B2

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