Sodium Cyanide → HCID 57386575, compound

HRID 2190453Notes

Reaction equation

HRID 2190453 reaction equation
Br[CH2:2][C:3]1[C:4]([Cl:13])=[C:5]([CH:10]=[CH:11][CH:12]=1)[C:6]([O:8][CH3:9])=[O:7].[C-:14]#[N:15].[Na+]>CN(C)C=O.C(OCC)(=O)C.CCCCCC>[Cl:13][C:4]1[C:3]([CH2:2][C:14]#[N:15])=[CH:12][CH:11]=[CH:10][C:5]=1[C:6]([O:8][CH3:9])=[O:7]

Participants

6

Reactant 2

HCID 8929Sodium CyanideHCID 57386060Benzoic acid, 3-(bromomethyl)-2-chloro-, methyl ester

Product 1

HCID 57386575HCID 57386575, compoundYield 79%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of methyl 3-(bromomethyl)-2-chlorobenzoate (748 mg, 2.84 mmol) in N,N-dimethylformamide (7 mL) was added sodium cyanide (412 mg, 8.41 mmol), and the mixture was stirred under a nitrogen stream at 80° C. for 1 hr. The reaction mixture was diluted with a mixed solvent of ethyl acetate and hexane (1:1). The solution was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and filtered. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=98/2→80/20) and crystallized from ethyl acetate/hexane to give the title compound (470 mg, 79%) as white crystals.

Workup

  1. washThe solution was washed with water and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customThe solvent was evaporated under reduced pressure
  5. customthe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=98/2→80/20)
  6. customcrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-c26f01914bba40f6afd375405423e8a9
Source dataset
uspto-grants-2012_12
Patent number
US08324395B2

Reaction notes

Loading…