Potassium Carbonate → HCID 89581067, compound

HRID 1501223Notes

Reaction equation

HRID 1501223 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:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[C:19]#[N:20].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:9]([O:8][C:6](=[O:7])[C:5]1[CH:13]=[CH:14][C:2]([O:15][C:16]2[CH:23]=[CH:22][CH:21]=[C:18]([C:19]#[N:20])[CH:17]=2)=[CH:3][CH:4]=1)([CH3:12])([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 133943-CyanophenolHCID 2736444Tert-butyl 4-fluorobenzoate

Product 1

HCID 89581067HCID 89581067, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

To the solution of tert-butyl 4-fluorobenzoate (500 mg, 2.55 mmol) and 3-hydroxybenzonitrile (306 mg, 2.55 mmol) in N,N-dimethylformamide (80 mL) was added potassium carbonate (528 mg, 3.8 mmol), the mixture was stirred at 130° C. for 1 hour under microwave. Then evaporated the solvent purified by column chromatography (silica gel, Petroleum ether/ethyl acetate=10:1) to give tert-butyl-4-(3-cyanophenoxy)benzoate (185 mg, 57%), as oil, 1H-NMR (300 MHz, CD3OD) δ 8.00 (m, 2H), 7.56 (m, 2H), 7.43 (m, 2H), 7.05 (m, 2H), 1.59 (s, 9H).

Workup

  1. customThen evaporated the solvent
  2. custompurified by column chromatography (silica gel, Petroleum ether/ethyl acetate=10:1)

Sources & evidence

ORD record
ord-a1f13de513bb4fca872980fa040b0765
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

Loading…