Bromoacetonitrile → HCID 14837015, compound

HRID 2106805Notes

Reaction equation

HRID 2106805 reaction equation
[CH:1]([N:4](C(C)C)CC)(C)[CH3:2].BrCC#N.[F:14][C:15]1[C:16]([OH:28])=[N:17][CH:18]=[C:19]([O:21][C:22]([F:27])([F:26])[CH:23]([F:25])[F:24])[CH:20]=1>C(Cl)Cl>[C:1]([CH2:2][N:17]1[CH:18]=[C:19]([O:21][C:22]([F:26])([F:27])[CH:23]([F:24])[F:25])[CH:20]=[C:15]([F:14])[C:16]1=[O:28])#[N:4]

Participants

5

Reactant 3

HCID 11534BromoacetonitrileHCID 81531DiisopropylethylamineHCID 178517845HCID 178517845, compound

Product 1

HCID 14837015HCID 14837015, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Diisopropylethylamine (0.82 ml, 4.7 mmol) and 0.30 ml (4.3 mmol) of bromoacetonitrile were added consecutively with stirring at ambient temperature to 3-fluoro-5-(1,1.2,2-tetrafluoroethoxy)-2-pyridinol (0.90 g, 3.98 mmol) in 5 ml of methylene chloride and the mixture allowed to react overnight. It was then diluted with 25 ml of methylene chloride, extracted with 25 ml of water and with dilute aqueous sodium carbonate, dried over sodium sulfate, and concentrated by evaporation under reduced pressure to obtain the title compound as a solid. This was recrystallized from toluene to obtain 0.92 g (86 percent of theory) of purified material melting at 75.5-77° C. The proton nmr spectrum was consistent with the assigned structure.

Workup

  1. customto react overnight
  2. extractionextracted with 25 ml of water and with dilute aqueous sodium carbonate
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-4c265d6afae6472590aaf47917247e5f
Source dataset
uspto-grants-1990_06
Patent number
US04931452

Reaction notes

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