Sodium Carbonate → 5-bromo-3,3-dimethyl-2,3-dihydro-1H-indol-2-one

HRID 9323Notes

Reaction equation

HRID 9323 reaction equation
[CH3:1][C:2]1([CH3:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]1=[O:11].C([O-])(=O)C.[Na+].[Br:18]Br.C(=O)([O-])[O-].[Na+].[Na+]>C(O)(=O)C.O>[Br:18][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[NH:4][C:3](=[O:11])[C:2]2([CH3:12])[CH3:1]

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 24408BromineHCID 3131003,3-Dimethyl-1,3-dihydro-indol-2-oneHCID 517045Sodium Acetate

Product 1

HCID 120527965-bromo-3,3-dimethyl-2,3-dihydro-1H-indol-2-oneYield 92%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Procedure

3,3-dimethyl-indol-2-one (0.65 g, 4.03 mmol) and sodium acetate (0.33 g, 4.07 mmol) were stirred in acetic acid (5 cm3) then bromine (0.66 g, 4.13 mmol) in acetic acid (5 cm3) was added drop-wise to the reaction mixture. The reaction was stirred for 50 min., then poured into water. The mixture was basified with sodium carbonate, extracted with ethyl acetate (×3), dried (MgSO4), filtered, and evaporated to give the subtitled compound (0.89 g, 92%) 1H NMR (DMSO-d6) δ 1.21 (s, 6 H), 6.76 (d, 1 H, J=8.22 Hz), 7.29 (dd, 1 H, J=2.12 Hz, 8.23 Hz), 7.49 (d, 1 H, J=2.03 Hz), 10.4 (s, 1H).

Workup

  1. extractionextracted with ethyl acetate (×3)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-1410de5373474c20b5b594a894ba44f8
Source dataset
uspto-grants-2006_08
Patent number
US07091234B2

Reaction notes

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