Bicyclo(2.2.1)heptane-2-methanol → HCID 66924204, compound

HRID 2177041Notes

Reaction equation

HRID 2177041 reaction equation
[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][CH:2]2[CH2:8][OH:9].[H-].[Na+].[F:12][C:13]1[CH:20]=[CH:19][CH:18]=[C:17](F)[C:14]=1[C:15]#[N:16]>CN(C)C=O>[F:12][C:13]1[CH:20]=[CH:19][C:18]([O:9][CH2:8][CH:2]2[CH2:3][CH:4]3[CH2:7][CH:1]2[CH2:6][CH2:5]3)=[CH:17][C:14]=1[C:15]#[N:16]

Participants

5

Reactant 3

HCID 21308Bicyclo(2.2.1)heptane-2-methanolHCID 24758Sodium hydrideHCID 746952,6-Difluorobenzonitrile

Product 1

HCID 66924204HCID 66924204, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 2-norbornane methanol (1.3 g, 10.3 mmol) in dimethylformamide was added to a cooled (0° C.) slurry of sodium hydride (450 mg, 11.33 mmol) in dimethylformamide under nitrogen atmosphere. The reaction mixture was slowly warned to room temperature, stirred for 1 hour. Again, cooled (0° C.), then a solution of 2,6-difluorobenzonitrile (1.58 g, 11.33 mmol) in dimethylfomamide was added, stirred overnight at room temperature. The reaction mixture was poured on crushed-ice water, stirred. The reaction mixture was extracted with ethyl acetate, dried, filtered and concentrated. Purification by silica gel chromatography (1:1 hexanes in dichloromethane) yielded 986 mg of 2-fluoro-5-(bicyclo[2.2.1]hept-2-ylmethoxy)benzonitrile.

Workup

  1. customwas slowly warned to room temperature
  2. stirringstirred overnight at room temperature
  3. additionThe reaction mixture was poured
  4. stirringstirred
  5. extractionThe reaction mixture was extracted with ethyl acetate
  6. customdried
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification by silica gel chromatography (1:1 hexanes in dichloromethane)

Sources & evidence

ORD record
ord-1b4d5bb112e8450287e1f5c9513a2c92
Source dataset
uspto-grants-2015_06
Patent number
US09067897B2

Reaction notes

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