N-bromobutanimide → 5-Bromo-4,6-difluoroindoline

HRID 338228Notes

Reaction equation

HRID 338228 reaction equation
[F:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][NH:6]2.[Br:12]N1C(=O)CCC1=O>C(#N)C>[Br:12][C:10]1[C:2]([F:1])=[C:3]2[C:7](=[CH:8][C:9]=1[F:11])[NH:6][CH2:5][CH2:4]2

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 162444494,6-Difluoro-2,3-dihydro-1H-indole

Product 1

HCID 838958425-Bromo-4,6-difluoroindolineYield 83%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 4,6-difluoroindoline (4.6 g, 29.8 mmol) in acetonitrile (50 mL) was added a solution of N-bromosuccinimide (3.68 g, 20.6 mmol) acetonitrile (30 mL) at 0° C. dropwise. The reaction was stirred for 30 minutes and quenched with saturated aqueous sodium bicarbonate solution and diluted with ethyl acetate. The layers were separated and the organic phases were dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash chromatography (0-60% ethyl acetate in petroleum ether) to give the title compound (4.0 g, 58% yield) as colorless oil

Workup

  1. customquenched with saturated aqueous sodium bicarbonate solution
  2. additiondiluted with ethyl acetate
  3. customThe layers were separated
  4. dry with materialthe organic phases were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (0-60% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-3c79293afe6a4d389402c07a59cecca4
Source dataset
uspto-grants-2014_11
Patent number
US08889730B2

Reaction notes

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