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

HRID 9319

Reaction equation

HRID 9319 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-f40b35095113458e955889004f700469
Source dataset
uspto-grants-2006_08
Patent number
US07091234B2

Linked notes

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