6-amino-3-bromo-2-fluorobenzonitrile → HCID 86662399, compound

HRID 389465Notes

Reaction equation

HRID 389465 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([F:10])[C:5]([Br:11])=[CH:4][CH:3]=1.F[B-](F)(F)F.[O:17]=[N+:18]=[O:19]>C(#N)C.[Cl-].[Na+].O>[NH2:1][C:2]1[C:3]([N+:18]([O-:19])=[O:17])=[CH:4][C:5]([Br:11])=[C:6]([F:10])[C:7]=1[C:8]#[N:9]

Participants

5

Reactant 2

HCID 27611996-amino-3-bromo-2-fluorobenzonitrileHCID 11073463Nitronium tetrafluoroborate

Product 1

HCID 86662399HCID 86662399, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

To a cooled (0° C.) solution of 6-amino-3-bromo-2-fluoro-benzonitrile (8.0 g, 37 mmol) in acetonitrile (40 mL) under nitrogen was added dropwise a solution of nitronium tetrafluoroborate in acetonitrile. The reaction mixture and stirred for 16 h at RT. The reaction mixture was treated with brine and extracted with ethyl acetate. The organic fraction was washed with water followed by brine and dried over anhydrous sodium sulfate, filtered and concentrated. Purification by column chromatography (10 to 20% ethyl acetate:hexanes) afforded 5.0 g (52%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 8.6 (d, J=6.9 Hz, 1H), 6.8-7.1 (br. s, 2H).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic fraction was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by column chromatography (10 to 20% ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-f71bab9a48a344959e0540a7a68dbbcc
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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