Isopropanol → HCID 66997049, compound

HRID 1465898Notes

Reaction equation

HRID 1465898 reaction equation
[CH3:1][CH:2]([OH:4])[CH3:3].[H-].[Na+].F[C:8]1[CH:9]=[C:10]([CH:13]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:15]=1)[C:11]#[N:12]>CN(C=O)C>[CH:2]([O:4][C:8]1[CH:9]=[C:10]([CH:13]=[C:14]([C:16]([F:17])([F:19])[F:18])[CH:15]=1)[C:11]#[N:12])([CH3:3])[CH3:1]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 24758Sodium hydrideHCID 5190373-Fluoro-5-(trifluoromethyl)benzonitrile

Product 1

HCID 66997049HCID 66997049, compoundYield 131.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
27.5 °C

Procedure

To a mixture of propan-2-ol (102.96 g 1.76 moles) in DMF (3200 mL, 8 V) at 5° C. was added NaH (122 g, 5.08 moles). The mixture was stirred for 2 hours. To this mixture 3-fluoro-5-(trifluoromethyl)benzonitrile (400, 2.1 moles) was added dropwise. The temperature of the mass was increased to 25 to 30° C. and maintained at same temperature for 1 hour. Reaction was monitored by HPLC. After completion, the reaction mixture was quenched with ice cold water and extracted with ethyl acetate. The ethyl acetate layer was washed with brine, dried over sodium sulfate and then concentrated under vacuum to give 530 g (2.31 moles; 110%) of 3-isopropoxy-5-(trifluoromethyl)benzonitrile, which was taken as such to next step with no further purification. HPLC purity—96.5% by area (a/a).

Workup

  1. temperaturemaintained at same temperature for 1 hour
  2. customReaction
  3. customAfter completion, the reaction mixture was quenched with ice cold water
  4. extractionextracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-f0c2f9bdfd7645ebb05c27ab50da36a3
Source dataset
uspto-grants-2015_04
Patent number
US08999996B2

Reaction notes

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