Potassium Carbonate → Methyl 3-cyano-4-isopropoxybenzoate

HRID 730370Notes

Reaction equation

HRID 730370 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([O-])([O-])=O.[K+].[K+].C(C(N)CBr)(O[C:23](C)([CH3:25])[CH3:24])=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:23]([CH3:25])[CH3:24])[C:6]([O:8][CH3:9])=[O:7])#[N:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11769089Methyl 3-cyano-4-hydroxybenzoateHCID 22273677Boc-aminoethyl bromide

Product 1

HCID 21956805Methyl 3-cyano-4-isopropoxybenzoateYield 109.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of compound 3 (5.000 g, 17 mmol) in DMF (15 mL) was added K2CO3 (3.51 g, 26 mmol) and Boc-2-amino ethyl bromide (4.56 g, 20.35 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 (4.08 g, 55%) as white solid.

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-093eb1cc91454082b03219828e2e222a
Source dataset
uspto-grants-2009_09
Patent number
US07582668B2

Reaction notes

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