Bromoacetonitrile → 2-(5-Bromo-4-fluoro-2-methylphenylamino)acetonitrile

HRID 337140Notes

Reaction equation

HRID 337140 reaction equation
[CH3:1][CH2:2][N:3](C(C)C)C(C)C.[Br:10][C:11]1[C:12]([F:19])=[CH:13][C:14]([CH3:18])=[C:15]([CH:17]=1)[NH2:16].BrCC#N>C1COCC1>[Br:10][C:11]1[C:12]([F:19])=[CH:13][C:14]([CH3:18])=[C:15]([NH:16][CH2:1][C:2]#[N:3])[CH:17]=1

Participants

5

Reactant 3

HCID 11534BromoacetonitrileHCID 81531DiisopropylethylamineHCID 27827865-Bromo-4-fluoro-2-methylaniline

Product 1

HCID 866632582-(5-Bromo-4-fluoro-2-methylphenylamino)acetonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Hunig's Base (6.15 mL) was added to 5-bromo-4-fluoro-2-methylaniline (Example 318a, 3.59 g) in THF (50 mL) at room temperature followed by bromoacetonitrile (2.451 mL). The reaction was heated to reflux overnight. The reaction was cooled to room temperature and concentrated. 2N HCl and DCM were added. The organic layer was separated and dried (MgSO4) and concentrated to give the subtitle compound as a solid (6.61 g).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux overnight
  3. concentrationconcentrated
  4. addition2N HCl and DCM were added
  5. customThe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0b79f3aa4feb4c28b0f4e610db4b0c35
Source dataset
uspto-grants-2014_11
Patent number
US08889692B2

Reaction notes

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