Sulfuric Acid → 4-Bromo-2-fluorobenzamide

HRID 538992Notes

Reaction equation

HRID 538992 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([F:10])[CH:3]=1.FC(F)(F)C(O)=[O:14].S(=O)(=O)(O)O>O>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]([NH2:7])=[O:14])=[C:4]([F:10])[CH:3]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 6422Trifluoroacetic acidHCID 7360294-Bromo-2-fluorobenzonitrile

Product 1

HCID 27733314-Bromo-2-fluorobenzamideYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 4-bromo-2-fluorobenzonitrile (1.00 g, 5.00 mmol), trifluoroacetic acid (3.5 mL, 45 mmol), and sulfuric acid (3.5 mL, 66 mmol) was stirred at ambient temperature for 4 hours, at 30° C. for 15 hours, and at 50° C. for 6 hours. After cooling to 0° C., water (20 mL) was added, and the resulting suspension was stirred at 0° C. for 1.5 hours. The solids were collected by vacuum filtration, rinsed with excess water, and dried to afford 4-bromo-2-fluorobenzamide (0.956 g, 88%) as an off-white solid which was carried on without further purification.

Workup

  1. filtrationThe solids were collected by vacuum filtration
  2. washrinsed with excess water
  3. customdried

Sources & evidence

ORD record
ord-fead0a54088144928f92d419c3a5fd34
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

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