Acetonitrile → HCID 70979516, compound

HRID 924675Notes

Reaction equation

HRID 924675 reaction equation
CCC([O-])(C)C.[K+].[Cl:8][C:9]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:10]=1[C:11]([O:13]C)=O.[C:23](#[N:25])[CH3:24]>C1(C)C=CC=CC=1.Cl.O.CCOC(C)=O>[Cl:8][C:9]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:10]=1[C:11](=[O:13])[CH2:24][C:23]#[N:25]

Participants

8

Reactant 3

HCID 6342AcetonitrileHCID 15010065Methyl 2-chloro-5-(trifluoromethyl)benzoateHCID 23683543Potassium t-amylate

Product 1

HCID 70979516HCID 70979516, compoundYield 83.4%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 1140TolueneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Potassium tert-pentoxide 1.7 M in toluene (7.35 mL, 12.5 mmol) was added drop wise to a solution of methyl 2-chloro-5-(trifluoromethyl)benzoate (2.0 g, 8.38 mmol) and ACN (1.32 mL, 25.15 mmol) in anhydrous toluene (30 mL). The mixture was stirred at room temperature for 20 min, then diluted with HCl 1 N (20 mL), water (75 mL) and EtOAc (100 mL). The organic layer was separated, washed with water (50 mL×2) and brine (50 mL×2), dried over sodium sulfate and concentrated. Column chromatography on silica gel (0 to 20% EtOAc/hexane) provided the title compound (1.73 g, 83%).

Workup

  1. customThe organic layer was separated
  2. washwashed with water (50 mL×2) and brine (50 mL×2)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-97ba49a2081c4670bdec06dd641b6f52
Source dataset
uspto-grants-2016_03
Patent number
US09283224B2

Reaction notes

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