3-Fluoroaniline → N-(3-fluorophenyl)-2-(4-methoxyphenyl)acetamide

HRID 907438Notes

Reaction equation

HRID 907438 reaction equation
CO[C:3](=[O:13])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1.[F:14][C:15]1[CH:16]=[C:17]([NH2:21])[CH:18]=[CH:19][CH:20]=1.[H-].[Na+]>CS(C)=O>[F:14][C:15]1[CH:16]=[C:17]([NH:21][C:3](=[O:13])[CH2:4][C:5]2[CH:6]=[CH:7][C:8]([O:11][CH3:12])=[CH:9][CH:10]=2)[CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 3

HCID 97423-FluoroanilineHCID 24758Sodium hydrideHCID 90266Methyl 4-methoxyphenylacetate

Product 1

HCID 765698N-(3-fluorophenyl)-2-(4-methoxyphenyl)acetamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Using the procedure for Example 22, (4-methoxy-phenyl)-acetic acid methyl ester Compound 22a was reacted with 3-fluoro-phenylamine and sodium hydride in DMSO at room temperature to provide N-(3-fluoro-phenyl)-2-(4-methoxy-phenyl)-acetamide Compound 23a. Compound 23a was reacted with borotribromide in dichloromethane to yield N-(3-fluoro-phenyl)-2-(4-hydroxy-phenyl)-acetamide Compound 23b.

Sources & evidence

ORD record
ord-84b4df770f5e40fc9d42806e5fcdafab
Source dataset
uspto-grants-2011_09
Patent number
US08013153B2

Reaction notes

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