Sodium Cyanide → HCID 66874991, compound

HRID 516868Notes

Reaction equation

HRID 516868 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([F:19])=[C:7]([CH:18]=1)[O:8][CH2:9][C:10]1[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][C:11]=1[CH3:17].[C-:20]#[N:21].[Na+]>CN(C=O)C>[CH3:17][C:11]1[CH:12]=[CH:13][CH:14]=[C:15]([CH3:16])[C:10]=1[CH2:9][O:8][C:7]1[CH:18]=[C:3]([CH2:2][C:20]#[N:21])[CH:4]=[CH:5][C:6]=1[F:19]

Participants

4

Reactant 2

HCID 8929Sodium CyanideHCID 66893102HCID 66893102, compound

Product 1

HCID 66874991HCID 66874991, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of 2-((5-(chloromethyl)-2-fluorophenoxy)methyl)-1,3-dimethylbenzene (Step C, 4 g, 14.3 mmol), KI (0.33 g) in DMF (30 ml) was added NaCN (1.02 g, 20.8 mmol). The reaction mixture was heated at 100° C. for 4 hours, concentrated, diluted with EtOAc and washed with water (2×), dried over Na2SO4, filtered, concentrated and purified by flash chromatography on a silica gel column (hexane:methylene chloride, 1:1) to give the title compound.

Workup

  1. concentrationconcentrated
  2. additiondiluted with EtOAc
  3. washwashed with water (2×)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by flash chromatography on a silica gel column (hexane:methylene chloride, 1:1)

Sources & evidence

ORD record
ord-ac415dfbd8df4a278a9a1fe14da4c89a
Source dataset
uspto-grants-2015_08
Patent number
US09115072B2

Reaction notes

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