Potassium Carbonate → 2-Cyclobutyloxy-3,4-dimethoxybenzonitrile

HRID 1004019Notes

Reaction equation

HRID 1004019 reaction equation
[OH:1][C:2]1[C:9]([O:10][CH3:11])=[C:8]([O:12][CH3:13])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH:14]1(Br)[CH2:17][CH2:16][CH2:15]1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH:14]1([O:1][C:2]2[C:9]([O:10][CH3:11])=[C:8]([O:12][CH3:13])[CH:7]=[CH:6][C:3]=2[C:4]#[N:5])[CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 78110BromocyclobutaneHCID 119947582-Hydroxy-3,4-dimethoxybenzonitrile

Product 1

HCID 184706162-Cyclobutyloxy-3,4-dimethoxybenzonitrileYield 75.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

2-Hydroxy-3,4-dimethoxybenzonitrile (6.65 g, 0.037 mol) was added to a suspension of cyclobutyl bromide (5.01 g, 0.037 mol) and potassium carbonate (5.11 g, 0.037 mol) in dimethylformamide (65 ml) and the reaction stirred at 80° C. for 4 hours. On cooling, the mixture was concentrated under reduced pressure and the residue partitioned between water (50 ml) and ethyl acetate (50 ml). The aqueous layer was extracted with further ethyl acetate (100 ml) and the combined organic extracts dried (MgSO4), filtered and evaporated under reduced pressure to give the subtitle compound as a brown oil (6.50 g, 75%). Rf 0.63 (dichloromethane). MS m/z 251 (MNH4)+.

Workup

  1. temperatureOn cooling
  2. concentrationthe mixture was concentrated under reduced pressure
  3. customthe residue partitioned between water (50 ml) and ethyl acetate (50 ml)
  4. extractionThe aqueous layer was extracted with further ethyl acetate (100 ml)
  5. dry with materialthe combined organic extracts dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-398ad501306c4ee182d84a9e366ef3fa
Source dataset
uspto-grants-2000_04
Patent number
US06048864

Reaction notes

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