Sulfuric Acid → 3-Chloro-4-fluoro-N-methylaniline

HRID 127822Notes

Reaction equation

HRID 127822 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9](C)[CH:10]=O)[CH:5]=[CH:6][C:7]=1[F:8].S(=O)(=O)(O)O>O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[F:8])[NH:9][CH3:10]

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 12876631N-(3-chloro-4-fluorophenyl)N-methylformamide

Product 1

HCID 128766323-Chloro-4-fluoro-N-methylaniline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
10 °C

Procedure

A mixture of 42.2 g of 5A and 50 g of concentrated sulfuric acid in 600 ml of water was refluxed for 7 hours. The resulting mixture was charcoaled, filtered, cooled to 10° C. and made alkaline with sodium hydroxide. The resulting mixture was extracted with ether. The extract was dried and the ether evaporated to give 3-chloro-4-fluoro-N-methyl-aniline, (5B), as a yellow oil.

Workup

  1. temperaturewas refluxed for 7 hours
  2. filtrationfiltered
  3. extractionThe resulting mixture was extracted with ether
  4. customThe extract was dried
  5. customthe ether evaporated

Sources & evidence

ORD record
ord-a95517720cb2420d9d6caa979bbb692f
Source dataset
uspto-grants-1981_03
Patent number
US04257805

Reaction notes

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