Sodium hydride → HCID 71295195, compound

HRID 868821Notes

Reaction equation

HRID 868821 reaction equation
[H-].[Na+].[CH:3]1([CH2:6][OH:7])[CH2:5][CH2:4]1.[Br:8][C:9]1[CH:10]=[CH:11][C:12](F)=[C:13]([CH:16]=1)[C:14]#[N:15]>CN(C=O)C>[Br:8][C:9]1[CH:10]=[CH:11][C:12]([O:7][CH2:6][CH:3]2[CH2:5][CH2:4]2)=[C:13]([CH:16]=1)[C:14]#[N:15]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 75644CyclopropanemethanolHCID 27249005-Bromo-2-fluorobenzonitrile

Product 1

HCID 71295195HCID 71295195, compoundYield 92.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
50 °C

Procedure

Sodium hydride, 60% suspension in oil (3.6 g, 0.09 mol), is added to a solution of cyclopropylmethanol (6.49 g, 0.09 mol) in dry DMF (200 ml) at 0° C. under nitrogen. After 30 min at 0° C., 5-bromo-2-fluorobenzonitrile (12.0 g, 0.06 mol) in dry DMF (50 ml) is added, and the reaction is stirred at 50° C. for 16 h. Ice-water (200 ml) is added to the reaction mixture, which is then extracted with ethyl acetate (2×200 ml). The organic phases are washed with water (2×200 ml) and saturated sodium chloride solution (1×200 ml) and dried over sodium sulfate. After removal of the solvent, the crude product is purified by chromatography, giving 14 g of a yellow oil;

Workup

  1. extractionis then extracted with ethyl acetate (2×200 ml)
  2. washThe organic phases are washed with water (2×200 ml) and saturated sodium chloride solution (1×200 ml)
  3. dry with materialdried over sodium sulfate
  4. customAfter removal of the solvent
  5. customthe crude product is purified by chromatography

Sources & evidence

ORD record
ord-349699eb17d144dab713106e68d0929d
Source dataset
uspto-grants-2015_03
Patent number
US08969335B2

Reaction notes

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