Bromine → 7-Bromo-5-nitroindoline

HRID 2086034Notes

Reaction equation

HRID 2086034 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH2:8][CH2:7]2)([O-:3])=[O:2].[Br:13]Br>CC(O)=O>[Br:13][C:11]1[CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[C:6]2[C:10]=1[NH:9][CH2:8][CH2:7]2

Participants

4

Reactant 2

HCID 24408BromineHCID 362195-Nitroindoline

Product 1

HCID 3234907-Bromo-5-nitroindolineYield 131.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 5-nitroindoline (from Aldrich, 2.0 g, 12.2 mmol) in 15 mL of AcOH was added Br2 (1.0 mL, 19.4 mmol) in a portion and the resulting solution was stirred for 1 h at 25° C. Reaction mixture was concentrated in vacuo, yielding a yellow solid (3.9 g, >95%) of the desired product as a HBr salt, which was subjected to the following reaction without further purification.

Workup

  1. customReaction mixture
  2. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-fd9a68f0e42b4ebcbb5e93808f0b67d8
Source dataset
uspto-grants-2004_04
Patent number
US06723741B2

Reaction notes

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