N-bromobutanimide → 942224-45-5

HRID 539709Notes

Reaction equation

HRID 539709 reaction equation
[F:1][C:2]1[C:11]([CH3:12])=[CH:10][CH:9]=[C:8]([F:13])[C:3]=1[C:4]([O:6][CH3:7])=[O:5].[Br:14]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.CC(N=NC(C#N)(C)C)(C#N)C>[Br:14][CH2:12][C:11]1[C:2]([F:1])=[C:3]([C:8]([F:13])=[CH:9][CH:10]=1)[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 55255639Methyl 2,6-difluoro-3-methylbenzoate

Product 1

HCID 58919229942224-45-5Yield 107%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To a room temperature solution of methyl 2,6-difluoro-3-methylbenzoate (9.35 g, 50.2 mmol, 1.0 equiv) and N-bromosuccinimide (11.6 g, 65.3 mmol, 1.3 equiv) in carbon tetrachloride (230 mL) was added catalytic AIBN (−200 mg) as a solid in one portion. The resulting reaction mixture was heated to reflux overnight. After the reaction mixture was allowed to cool to room temperature, it was washed with aq. satd. NaHCO3. The aqueous layer was extracted with dichloromethane, and the combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to provide 14.24 g (>100% mass recovery) of unpurified bromide, which was taken on to the next step without purification.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas heated
  3. temperatureto reflux overnight
  4. washit was washed with aq. satd
  5. extractionThe aqueous layer was extracted with dichloromethane
  6. dry with materialthe combined organic layers were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5b5f5e221e874a38b99d6a678d926509
Source dataset
uspto-grants-2014_10
Patent number
US08871768B2

Reaction notes

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