Hydrochloric Acid → HCID 68757557, compound

HRID 1753979Notes

Reaction equation

HRID 1753979 reaction equation
F[C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:14])([F:13])[F:12])[C:3]=1[C:4]([NH2:6])=[O:5].C[Si](C)(C)[O-:17].[K+].Cl>COCCOCCOC>[OH:17][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]([C:11]([F:14])([F:13])[F:12])[C:3]=1[C:4]([NH2:6])=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 27375422-Fluoro-6-(trifluoromethyl)benzamideHCID 23668039Potassium trimethylsilanolate

Product 1

HCID 68757557HCID 68757557, compound

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 2-fluoro-6-(trifluoromethyl)benzamide (500 mg, 2.41 mmol) in diglyme (8.05 mL) was added potassium trimethylsilanolate (1.08 g, 8.45 mmol). The reaction mixture was stirred at 120° C. overnight. The reaction mixture was acidified with 1N HCl (30 mL) and extracted with EtOAc (3×10 mL). The combined organic layers were washed with 10% solution of LiCl in water, dried with MgSO4, filtered and evaporated under reduced pressure. The resulting residue was purified by Combiflash™ chromatography (SiO2, 12 g, elution with 20-40% EtOAc/hexanes over 40 min) to afford the title compound as solid.

Workup

  1. extractionextracted with EtOAc (3×10 mL)
  2. washThe combined organic layers were washed with 10% solution of LiCl in water
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe resulting residue was purified by Combiflash™ chromatography (SiO2, 12 g, elution with 20-40% EtOAc/hexanes over 40 min)

Sources & evidence

ORD record
ord-cd51e396cece4a768396daa6ed2dd6fa
Source dataset
uspto-grants-2015_10
Patent number
US09168248B2

Reaction notes

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