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

HRID 9319

反応式

HRID 9319 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-f40b35095113458e955889004f700469
出典データセット
uspto-grants-2006_08
特許番号
US07091234B2

関連ノート

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