Bromine → 5-Bromo-spiro [cyclopentane-1,3'-[3h]indol]-2'(1'h)-one

HRID 496673

반응식

HRID 496673 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]2([CH2:13][CH2:12][CH2:11][CH2:10]2)[C:2]1=[O:14].C([O-])(=O)C.[Na+].[Br:20]Br.C(=O)([O-])O.[Na+]>C(O)(=O)C>[Br:20][CH:13]1[C:3]2([C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][C:2]2=[O:14])[CH2:10][CH2:11][CH2:12]1

참가 물질

6

반응물 4

HCID 24408BromineHCID 3633431',2'-Dihydrospiro[cyclopentane-1,3'-indole]-2'-oneHCID 516892Sodium BicarbonateHCID 517045Sodium Acetate

생성물 1

HCID 219862275-Bromo-spiro [cyclopentane-1,3'-[3h]indol]-2'(1'h)-one수율 105%

시약·촉매·용매 1

HCID 176Acetic Acid용매2회

실험 절차

A solution of spiro[cyclopentane-1,3′-[3H]indol]-2′(1′H)-one (0.27 g, 1.4 mmol) and sodium acetate (0.12 g, 1.46 mmol) in acetic acid (10 cm3) was treated with bromine (0.24 g, 1.51 mmol) in acetic acid (2 cm3). After 30 min. the mixture was poured into sat. sodium hydrogen carbonate solution and extracted with EtOAc (×2), the combined organic layers were washed with water, sat. sodium hydrogen carbonate solution, water, dried (MgSO4), and evaporated to give the subtitled compound (0.37 g, 1.47 mmol, 96%) as an off-white solid which was used without further purification: 1H NMR (CDCl3) δ 1.8-2.27 (m, 8H), 6.79 (d, J=8 Hz, 1H), 7.30-7.39 (m, 2H), 8.63 (br s, 1H).

후처리

  1. extractionextracted with EtOAc (×2)
  2. washthe combined organic layers were washed with water, sat. sodium hydrogen carbonate solution, water
  3. dry with materialdried (MgSO4)
  4. customevaporated

출처 및 근거

ORD 기록
ord-a4dd9afee25b403186493824ecb8e962
출처 데이터셋
uspto-grants-2005_09
특허 번호
US06946454B2

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