Water → 3-Bromo-2-fluoro-5-nitrobenzonitrile

HRID 389466Notes

Reaction equation

HRID 389466 reaction equation
N[C:2]1[C:9]([N+:10]([O-:12])=[O:11])=[CH:8][C:7]([Br:13])=[C:6]([F:14])[C:3]=1[C:4]#[N:5].N(OC(C)(C)C)=O.O>O1CCCC1>[Br:13][C:7]1[C:6]([F:14])=[C:3]([CH:2]=[C:9]([N+:10]([O-:12])=[O:11])[CH:8]=1)[C:4]#[N:5]

Participants

5

Reactant 3

HCID 962WaterHCID 10906Tert-Butyl nitriteHCID 86662399HCID 86662399, compound

Product 1

HCID 667600553-Bromo-2-fluoro-5-nitrobenzonitrileYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a cooled (0° C.) solution of 2-amino-5-bromo-6-fluoro-3-nitro-benzonitrile (8.0 g, 30.8 mmol) in tetrahydrofuran (40 mL) was added tert-butyl nitrite (4.6 mL, 37 mmol) dropwise and stirred for 16 h at 50° C. The reaction mixture was treated with water and extracted with ethyl acetate. The organic fraction was washed with water and brine, dried over sodium sulfate, filtered, and concentrated. Purification by column chromatography (2% to 10% ethyl acetate:hexanes) afforded 4.0 g (53%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 8.72 (dd, J=3.0, 2.7 Hz, 1H), 8.51 (dd, J=3.0, 2.7 Hz, 1H).

Workup

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

Sources & evidence

ORD record
ord-1939ce7545e848309d9de087f932eb13
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

Loading…