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

HRID 1198934Notes

Reaction equation

HRID 1198934 reaction equation
[Br:1]Br.[CH3:3][C:4]1([CH3:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][C:5]1=[O:13].C([O-])(=O)C.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>C(O)(=O)C>[CH3:3][C:4]1([CH3:14])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Br:1])[CH:11]=2)[NH:6][C:5]1=[O:13]

Participants

6

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-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of bromine (1.98 g) in acetic acid (10 cm3) was added dropwise to a stirred solution of 3,3-dimethyl-indol-2-one (2.0 g) and sodium acetate (1.01 g) in acetic acid (10 cm3). The mixture was stirred at room temperature for 30 minutes, poured onto water (20 cm3), basified to pH9 with sodium carbonate, and extracted with ethyl acetate (3×50 cm3). The combined and dried (MgSO4) organic extracts were evaporated in vacuo and the residue chromatographed on silica (Merck "MK 60.9385" [Trade Mark]) eluting with methanol:hexane:dichloromethane, 1:10:40 by volume. Combination and evaporation of the appropriate fractions gave the title compound, m.p. 166°-166.5° (2.15 g).

Workup

  1. additionpoured onto water (20 cm3)
  2. extractionextracted with ethyl acetate (3×50 cm3)
  3. dry with materialdried (MgSO4) organic extracts
  4. customwere evaporated in vacuo
  5. customthe residue chromatographed on silica (Merck "MK 60.9385" [Trade Mark])
  6. washeluting with methanol
  7. customCombination and evaporation of the appropriate fractions

Sources & evidence

ORD record
ord-c6524b09150c46ab82236ffe848ee577
Source dataset
uspto-grants-1990_02
Patent number
US04898872

Reaction notes

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