Sulfuric Acid → HCID 66606809, compound

HRID 717148Notes

Reaction equation

HRID 717148 reaction equation
[Br:1][C:2]1[C:9]([CH3:10])=[CH:8][C:5]([C:6]#[N:7])=[C:4]([F:11])[CH:3]=1.S(=O)(=O)(O)[OH:13]>C(O)(C(F)(F)F)=O>[Br:1][C:2]1[C:9]([CH3:10])=[CH:8][C:5]([C:6]([NH2:7])=[O:13])=[C:4]([F:11])[CH:3]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 341754194-Bromo-2-fluoro-5-methylbenzonitrile

Product 1

HCID 66606809HCID 66606809, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-bromo-2-fluoro-5-methylbenzonitrile (40 g, 190 mmol) in a mixture of sulfuric acid (98%) and TFA (v/v=4:1, 480 mL) was stirred at 80° C. for 16 h. After the mixture was cooled to room temperature, the resulting mixture was poured into ice-cold water. The resulting precipitate was collected by filtration, washed with water and dried under reduced pressure to give the title compound (41 g, 95% yield) as a white solid. MS (ESI) m/z 232.0 [M+1]+.

Workup

  1. temperatureAfter the mixture was cooled to room temperature
  2. additionthe resulting mixture was poured into ice-cold water
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with water
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-94b0c82a336045c78c5e9283521b894c
Source dataset
uspto-grants-2015_11
Patent number
US09193692B2

Reaction notes

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