Trifluoroacetic acid → 3-Bromo-6-fluoro-2-methylbenzonitrile

HRID 1466066Notes

Reaction equation

HRID 1466066 reaction equation
C1C(=O)N([Br:8])C(=O)C1.[F:9][C:10]1[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[C:11]=1[C:12]#[N:13].C(O)(C(F)(F)F)=O>>[Br:8][C:15]1[C:14]([CH3:18])=[C:11]([C:10]([F:9])=[CH:17][CH:16]=1)[C:12]#[N:13]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 67184N-bromobutanimideHCID 186771512-Fluoro-6-methylbenzonitrile

Product 1

HCID 666438523-Bromo-6-fluoro-2-methylbenzonitrile

Procedure

NBS (265 g, 1490 mmol) was added portion wise to a stirred, cooled room temperature mixture of 2-Fluoro-6-methylbenzonitrile (191.8 g, 1419 mmol) in TFA (553 mL, 8500 mmol) and then the mixture was heated at reflux for 48 hours. The reaction was poured into 1 L of ice, diluted with 700 mL 30% EtOAc/Hexanes, and agitated. The aqueous layer was cut, and the organic layers were washed with 1N NaOH twice and with water. The organic layers were dried over Na2SO4, concentrated, and then stored in a −10° C. freezer overnight. The resulting crystals were filtered and washed with 5% EtOAc/Hexanes to yield the title product.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 48 hours
  3. washthe organic layers were washed with 1N NaOH twice
  4. dry with materialThe organic layers were dried over Na2SO4
  5. concentrationconcentrated
  6. filtrationThe resulting crystals were filtered
  7. washwashed with 5% EtOAc/Hexanes

Sources & evidence

ORD record
ord-0efe8b92e436491380308e7b7f9739b1
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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