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

HRID 236441

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

Reactant 4

HCID 807Iodine

HCID 77231-Chloro-4-(chloromethyl)benzene

HCID 517045Sodium Acetate

HCID 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 as described in Example III. Yield 25.8 grams (74 percent), boiling point 162°-170° C. at 0.13 mmHg.

Sources & evidence

ORD record: ord-ec17b135791349aa87589d5aa58776f1
Source dataset: uspto-grants-1987_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04644082

Linked notes

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