Potassium Carbonate → HCID 89580563, compound

HRID 1501229Notes

Reaction equation

HRID 1501229 reaction equation
F[C:2]1[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[CH:4][CH:3]=1.[OH:15][C:16]1[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:20]([C:19]1[CH:22]=[CH:23][C:16]([O:15][C:2]2[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[CH:4][CH:3]=2)=[CH:17][CH:18]=1)#[N:21]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 130194-CyanophenolHCID 2736444Tert-butyl 4-fluorobenzoate

Product 1

HCID 89580563HCID 89580563, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of tert-butyl 4-fluorobenzoate (392 mg, 2 mmol) in dimethyl formamide (20 mL) was added 4-hydroxybenzonitrile (240 mg, 2 mmol) and potassium carbonate (552 mg, 4 mmol), the mixture was heated to 130° C. for 0.5 hour by microwave (pressure: 3.2 bar, equipment power: 150 W). The solvent was evaporated in vacuo and purified by column chromatography (silica gel, dichloromethane/methanol=20:1) to give tert-butyl 4-(4-cyanophenoxy)benzoate (80 mg, 14%). LRMS (M+H+) m/z: calcd 295.12. found 295.

Workup

  1. customThe solvent was evaporated in vacuo
  2. custompurified by column chromatography (silica gel, dichloromethane/methanol=20:1)

Sources & evidence

ORD record
ord-af25a79d509f4fee95020ea254c33cc6
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

Loading…