Water → 5-Fluoro-2-nitroanisole

HRID 496556Notes

Reaction equation

HRID 496556 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([OH:8])[CH:7]=1.IC.[C:14](=O)([O-])[O-].[Cs+].[Cs+].O>CN(C=O)C>[CH3:14][O:8][C:6]1[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=1[N+:9]([O-:11])=[O:10]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 99375-Fluoro-2-nitrophenolHCID 10796Cesium carbonate

Product 1

HCID 27792505-Fluoro-2-nitroanisole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3 g of 5-fluoro-2-nitrophenol are dissolved in DMF and, after addition of 1.1 equivalent each of iodomethane and cesium carbonate, stirred at room temperature. After the reaction is complete, the reaction mixture is poured into water, extracted with diethyl ether, washed and concentrated. 3.2 g of 2-methoxy-4-fluoronitro-benzene are produced. Starting from this, 4.2 g of 2-methoxy-4-pyrrolidinylnitrobenzene are prepared by reaction with pyrrolidine by general reaction method A. The crude product is hydrogenated by general method B. 3.6 g of 2-methoxy-4-pyrrolidinylaminobenzene are obtained. Starting from 150 mg of the crude product and by reaction with 2-thiophenesulfonyl chloride, 154 mg of thiophene-2-sulfonic acid 2-methoxy-4-pyrrolidin-1-ylphenylamide are prepared by general method C.

Workup

  1. extractionextracted with diethyl ether
  2. washwashed
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-006c48034f794f689b056c515d220216
Source dataset
uspto-grants-2005_09
Patent number
US06946466B2

Reaction notes

Loading…