Sulfuric Acid → 4-Bromo-2-fluorobenzamide

HRID 717193Notes

Reaction equation

HRID 717193 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([F:10])[CH:3]=1.C(O)(C(F)(F)F)=[O:12].S(=O)(=O)(O)O>>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]([NH2:7])=[O:12])=[C:4]([F:10])[CH:3]=1

Participants

4

Reactant 3

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

Product 1

HCID 27733314-Bromo-2-fluorobenzamideYield 87.4%

Procedure

A solution of 4-bromo-2-fluorobenzonitrile (10.0 g, 50.0 mmol) in a 70 mL mixture of TFA (56.0 mL, 727 mmol)-sulfuric acid (14.0 mL, 263 mmol) (4:1 VAT) was stirred at 40° C. for 16 h. The reaction was poured while still warm over ice water. The product precipitated and the solid was filtered and dried to give 4-bromo-2-fluorobenzamide (9.53 g, 43.7 mmol, 87% yield) as a white solid. MS (ESI) m/z 218.1 [M]+, 220.1 [M+2]+.

Workup

  1. additionThe reaction was poured
  2. customThe product precipitated
  3. filtrationthe solid was filtered
  4. customdried

Sources & evidence

ORD record
ord-f6d24211168c46d581de4e740cbce5dc
Source dataset
uspto-grants-2015_11
Patent number
US09193692B2

Reaction notes

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