Sodium Cyanide → Dimethyl 2-(cyanomethyl)-5-(propan-2-yloxy)benzene-1,3-dicarboxylate

HRID 577438Notes

Reaction equation

HRID 577438 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:13]=[C:12]([O:14][CH:15]([CH3:17])[CH3:16])[CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[C:5]=1[CH2:18]Br.[C-:21]#[N:22].[Na+]>CS(C)=O.O>[C:21]([CH2:18][C:5]1[C:4]([C:3]([O:2][CH3:1])=[O:20])=[CH:13][C:12]([O:14][CH:15]([CH3:17])[CH3:16])=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8])#[N:22]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 86723676Dimethyl 2-(bromomethyl)-5-propan-2-yloxybenzene-1,3-dicarboxylate

Product 1

HCID 86723678Dimethyl 2-(cyanomethyl)-5-(propan-2-yloxy)benzene-1,3-dicarboxylateYield 87%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent2×

Procedure

To a solution of 2-bromomethyl-5-isopropoxy-isophthalic acid dimethyl ester (Cpd C, 17.4 g, 50.5 mmol) in DMSO (200 mL) was added NaCN (3.71 g, 75.7 mmol) in H2O (20 mL). The resulting reaction mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into water (500 mL), and extracted with ethyl acetate (2×300 mL). The combined organic phases were washed with brine (1×300 mL), dried over sodium sulfate, concentrated under vacuum, and purified by column chromatography (0-40%, EtOAc/heptanes) to give Dimethyl 2-(cyanomethyl)-5-(propan-2-yloxy)benzene-1,3-dicarboxylate (Cpd D, 12.8 g, 87% yield) as a clear oil which solidified upon standing.

Workup

  1. customThe resulting reaction mixture
  2. extractionextracted with ethyl acetate (2×300 mL)
  3. washThe combined organic phases were washed with brine (1×300 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under vacuum
  6. custompurified by column chromatography (0-40%, EtOAc/heptanes)

Sources & evidence

ORD record
ord-7599c950cf6f47798e5610034c9bda5d
Source dataset
uspto-grants-2015_05
Patent number
US09040515B2

Reaction notes

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