Iodine → N-methyl-N-p-chlorobenzyl-m-fluoroaniline

HRID 1980337Notes

Reaction equation

HRID 1980337 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([F:9])[CH:4]=1.[Cl:10][C:11]1[CH:18]=[CH:17][C:14]([CH2:15]Cl)=[CH:13][CH:12]=1.C([O-])(=O)C.[Na+].II>>[CH3:1][N:2]([CH2:15][C:14]1[CH:17]=[CH:18][C:11]([Cl:10])=[CH:12][CH:13]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([F:9])[CH:4]=1

Participants

5

Reactant 4

HCID 807IodineHCID 77231-Chloro-4-(chloromethyl)benzeneHCID 517045Sodium AcetateHCID 27590113-fluoro-N-methylaniline

Product 1

HCID 14008649N-methyl-N-p-chlorobenzyl-m-fluoroaniline

Procedure

N-methyl-N-p-chlorobenzyl-m-fluoroaniline was prepared from 17.5 grams (0.14 mole) of N-methyl-m-fluoroaniline, 23.7 grams (0.14 mole) p-chlorobenzyl chloride (Aldrich), 11.9 grams anhydrous sodium acetate and 0.12 grams iodine according to the procedure was described in Example III. Yield 25.8 grams (74 percent), boiling point 162°-170° C. at 0.13 mmHg.

Sources & evidence

ORD record
ord-4571d56f48264dc99820be6e8d338d52
Source dataset
uspto-grants-1985_04
Patent number
US04508803

Reaction notes

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