Cyclohexanol → HCID 86681309, compound

HRID 1778864Notes

Reaction equation

HRID 1778864 reaction equation
[CH:1]1([OH:7])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[Br:10][C:11]1[CH:18]=[CH:17][CH:16]=[C:15](F)[C:12]=1[C:13]#[N:14]>CN(C)C=O.C(OCC)(=O)C>[Br:10][C:11]1[CH:18]=[CH:17][CH:16]=[C:15]([O:7][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[C:12]=1[C:13]#[N:14]

Participants

6

Reactant 3

HCID 7966CyclohexanolHCID 24758Sodium hydrideHCID 27831392-Bromo-6-fluorobenzonitrile

Product 1

HCID 86681309HCID 86681309, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of cyclohexanol (0.275 g) in N,N-dimethylformamide (5 mL) was added sodium hydride (60%, 0.069 g). After 30 minutes, 2-bromo-6-fluorobenzonitrile (0.500 g) was added and the reaction stirred at room temperature for 2 hours. The reaction mixture was diluted with ethyl acetate (25 mL), washed with water (20 mL) and brine (20 mL), dried over magnesium sulfate, filtered, and concentrated. Silica gel chromatography eluting with a gradient of 3% to 10% ethyl acetate/hexanes provided the title compound.

Workup

  1. washwashed with water (20 mL) and brine (20 mL)
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. washSilica gel chromatography eluting with a gradient of 3% to 10% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-944c48149e734c65b0599e0e2a1676e2
Source dataset
uspto-grants-2016_02
Patent number
US09266877B2

Reaction notes

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