Ethyl 2-(4-bromo-2-nitrophenyl)acetate → 6-bromo-2,3-dihydro-1H-indol-2-one

HRID 1386349Notes

Reaction equation

HRID 1386349 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][C:7]=1[N+:13]([O-])=O)C>C(O)(=O)C.[Fe]>[Br:12][C:9]1[CH:8]=[C:7]2[C:6]([CH2:5][C:4](=[O:3])[NH:13]2)=[CH:11][CH:10]=1

Participants

4

Reactant 1

HCID 23247724Ethyl 2-(4-bromo-2-nitrophenyl)acetate

Product 1

HCID 27732896-bromo-2,3-dihydro-1H-indol-2-oneYield 43%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

Using a procedure analogous to that described for the starting material in Example 57, ethyl(4-bromo-2-nitrophenyl)acetate (26 g, 90 mmol) was treated with iron in acetic acid. The product thus obtained was recystallised from ether/isohexanes to give 6-bromooxindole (8.2 g, 42%).

Workup

  1. customThe product thus obtained

Sources & evidence

ORD record
ord-f7fae3e4e5694ee78bf254612174d1f3
Source dataset
uspto-grants-2001_07
Patent number
US06265411B1

Reaction notes

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