4-Bromo-2-fluoro-3-methylbenzonitrile → 4-Bromo-2-fluoro-3-methylbenzamide

HRID 1047289Notes

Reaction equation

HRID 1047289 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([F:10])[C:3]=1[CH3:11].C(O)(C(F)(F)F)=[O:13].S(=O)(=O)(O)O>O>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]([NH2:7])=[O:13])=[C:4]([F:10])[C:3]=1[CH3:11]

Participants

4

Reactant 2

HCID 595569134-Bromo-2-fluoro-3-methylbenzonitrileHCID 86586073TFA sulfuric acid

Product 1

HCID 666066774-Bromo-2-fluoro-3-methylbenzamideYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-Bromo-2-fluoro-3-methylbenzonitrile (11 g, 51.4 mmol) in a 100 mL mixture of TFA-sulfuric acid (4:1, V/V) was stirred at 40° C. for 16 h. After complete conversion of starting material, the reaction mixture was poured into iced-cold water. The resulting solid was filtered off and washed with water and dried to give the desired product (11.24 g, 48.4 mmol, 94% yield) as a white solid. MS (ESI) m/z 234.1 [M+2]+.

Workup

  1. filtrationThe resulting solid was filtered off
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-d1dfb64bb1a740c88fef8e63e507747e
Source dataset
uspto-grants-2013_10
Patent number
US08569494B2

Reaction notes

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