Triethylamine → N-(5-bromo-2,4-difluorophenyl)-2-methylpropanamide

HRID 1269174Notes

Reaction equation

HRID 1269174 reaction equation
[Br:1][C:2]1[C:3]([F:10])=[CH:4][C:5]([F:9])=[C:6]([CH:8]=1)[NH2:7].C(N(CC)CC)C.[C:18](Cl)(=[O:22])[CH:19]([CH3:21])[CH3:20]>C1COCC1>[Br:1][C:2]1[C:3]([F:10])=[CH:4][C:5]([F:9])=[C:6]([NH:7][C:18](=[O:22])[CH:19]([CH3:21])[CH3:20])[CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62325Isobutyryl chlorideHCID 27832955-Bromo-2,4-difluoroaniline

Product 1

HCID 16757161N-(5-bromo-2,4-difluorophenyl)-2-methylpropanamideYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into a solution of 2.6 g (12.6 mmol) of 5-bromo-2,4-difluoroaniline and 2.1 mL (15.1 mmol) of triethylamine in 50 mL THF at 0° C. was slowly added 1.6 mL (15.1 mmol) of isobutyryl chloride. The reaction mixture was stirred at room temperature for 2 hours and concentrated in vacuo. The residue was dissolved in EtOAc and washed with H2O, saturated aqueous Na2CO3 and brine. The organic layer was dried over MgSO4 and concentrated in vacuo to give 3.3 g (11.8 mmol, 94%) of N-(5-bromo-2,4-difluorophenyl)-2-methylpropanamide: ESMS m/e: 278.1 (M+H)+.

Workup

  1. customat 0° C.
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with H2O, saturated aqueous Na2CO3 and brine
  5. dry with materialThe organic layer was dried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cd842e07ce064aa2af7191fd639a8802
Source dataset
uspto-grants-2007_04
Patent number
US07199135B2

Reaction notes

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