Sodium Cyanide → 2-(3-(2,6-Dimethylbenzyloxy)-4-methoxyphenyl)acetonitrile

HRID 337251Notes

Reaction equation

HRID 337251 reaction equation
Br[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([O:19][CH3:20])=[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-:21]#[N:22].[Na+]>CN(C=O)C.CCOC(C)=O>[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:21]#[N:22])[CH:4]=[CH:5][C:6]=1[O:19][CH3:20]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 669586602-((5-(Bromomethyl)-2-methoxyphenoxy)methyl)-1,3-dimethylbenzene

Product 1

HCID 669590872-(3-(2,6-Dimethylbenzyloxy)-4-methoxyphenyl)acetonitrile

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The solution of 2-((5-(bromomethyl)-2-methoxyphenoxy)methyl)-1,3-dimethylbenzene (Step D, 3.28 g, 9.7 mmol) and NaCN (0.624 g, 12.7 mmol) in dry DMF (20 ml) was heated at 120° C. for 2.5 hours then cooled and diluted with EtOAc (50 ml). The organic layer was washed with water (30 ml), brine, dried over Na2SO4, filtered, concentrated, and purified by flash chromatography on a silica gel column (hex: ethyl acetate 2:1) to give the title compound.

Workup

  1. temperaturethen cooled
  2. washThe organic layer was washed with water (30 ml), brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by flash chromatography on a silica gel column (hex: ethyl acetate 2:1)

Sources & evidence

ORD record
ord-5f5a684092fb4797897fd13a6a70c1da
Source dataset
uspto-grants-2014_11
Patent number
US08889724B2

Reaction notes

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