Ethyl bromoacetate → Methyl 3-cyano-4-isopropoxybenzoate

HRID 222916Notes

Reaction equation

HRID 222916 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[OH:13])[C:6]([O:8][CH3:9])=[O:7])#[N:2].[C:14]([O-])([O-])=O.[K+].[K+].BrCC(O[CH2:25][CH3:26])=O>CN(C=O)C.O>[C:1]([C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[O:13][CH:25]([CH3:26])[CH3:14])[C:6]([O:8][CH3:9])=[O:7])#[N:2]

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 11769089Methyl 3-cyano-4-hydroxybenzoate

Product 1

HCID 21956805Methyl 3-cyano-4-isopropoxybenzoateYield 189.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of compound 3 (2.66 g, 7.27 mmol) in DMF (15 mL) was added K2CO3 (2.00 g, 15 mmol) and ethyl bromoacetate (1.61 mL, 14.5 mmol). The resulting mixture was stirred at 60° C. for three hours. The mixture was diluted with water and extracted with EtOAc (3×50 mL). The organic layers were combined, dried over Na2SO4, and concentrated. Purification with column chromatography (hexanes/EtOAc 50:50) gave the product 4 (3.02 g, 91%).

Workup

  1. extractionextracted with EtOAc (3×50 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customPurification with column chromatography (hexanes/EtOAc 50:50)

Sources & evidence

ORD record
ord-f7ed78ee3d0648d4873474d89b9f442c
Source dataset
uspto-grants-2012_06
Patent number
US08207340B2

Reaction notes

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