Ethyl Acetate → 6-bromo-2,3-dihydro-1H-indol-2-one

HRID 2096956Notes

Reaction equation

HRID 2096956 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9](O)=[O:10])=[C:4]([N+:12]([O-])=O)[CH:3]=1.C(OCC)(=O)C>C(O)(=O)C.[Fe]>[Br:1][C:2]1[CH:3]=[C:4]2[C:5]([CH2:8][C:9](=[O:10])[NH:12]2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 2715514-Bromo-2-nitrophenylacetic Acid

Product 1

HCID 27732896-bromo-2,3-dihydro-1H-indol-2-oneYield 58%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

Iron (40.0 g, 700 mmol) was added slowly to a stirred solution of 2-(4-bromo-2-nitrophenyl)acetic acid (preparation 1b, 46.6 g, 200 mmol) in acetic acid (390 mL) at 75° C., and then mixture was stirred for 1 hour at 100° C. Then the mixture was cooled and ethyl acetate was added. The mixture was filtered through Celite® and the solvent evaporated. The crude product was washed with 0.1M aqueous hydrochloric acid, water, diethyl ether and dried to give the title compound (22.0 g, 58%) as a solid.

Workup

  1. temperatureThen the mixture was cooled
  2. filtrationThe mixture was filtered through Celite®
  3. customthe solvent evaporated
  4. washThe crude product was washed with 0.1M aqueous hydrochloric acid, water, diethyl ether
  5. customdried

Sources & evidence

ORD record
ord-88c9bcda499f475eaee45a18a8e34477
Source dataset
uspto-grants-2013_05
Patent number
US08450341B2

Reaction notes

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