Potassium Carbonate → HCID 22461733, compound

HRID 1937776Notes

Reaction equation

HRID 1937776 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:6]=1[OH:13])=[O:4].[N+:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1F)([O-:16])=[O:15].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[N+:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[O:13][C:6]1[CH:7]=[C:8]([O:11][CH3:12])[CH:9]=[CH:10][C:5]=1[C:3]([O:2][CH3:1])=[O:4])([O-:16])=[O:15]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 738951-Fluoro-2-nitrobenzeneHCID 79523Methyl 4-methoxysalicylate

Product 1

HCID 22461733HCID 22461733, compoundYield 100.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2-methoxycarbonyl-5-methoxyphenol (34.1 g, 0.187 mol), 2-nitrofluorobenzene (19.7 mL, 0.187 mol), and K2CO3 (65 g, 0.467 mol) in DMF (200 mL) was heated at 110° C. for 18 h. The solution was diluted with water (200 mL) and extracted with EtOAc. The EtOAc layer was concentrated to give the crude title compound (57 g)which was used as is for the next step without further purification.

Workup

  1. extractionextracted with EtOAc
  2. concentrationThe EtOAc layer was concentrated

Sources & evidence

ORD record
ord-11d774f026004164b3b3b409bf240df1
Source dataset
uspto-grants-2002_05
Patent number
US06395919B1

Reaction notes

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