3-Fluoro-4-methylaniline → 3-Fluoro-4-methylphenyl methyl sulfide

HRID 2393039

Reaction equation

HRID 2393039 reaction equation
N(OC(C)(C)C)=O.[F:8][C:9]1[CH:10]=[C:11]([CH:13]=[CH:14][C:15]=1[CH3:16])N.[CH3:17][S:18]SC>C(Cl)(Cl)Cl>[F:8][C:9]1[CH:10]=[C:11]([S:18][CH3:17])[CH:13]=[CH:14][C:15]=1[CH3:16]

Participants

5

Reactant 3

HCID 99573-Fluoro-4-methylaniline2×HCID 10906Tert-Butyl nitrite2×HCID 12232Dimethyl Disulfide

Product 1

HCID 534144923-Fluoro-4-methylphenyl methyl sulfide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

t-Butyl nitrite (4 ml) was added to a mixture of 3-fluoro-4-methylaniline (5 g) and dimethyldisulphide (36 ml) in chloroform. After the reaction had initiated t-butyl nitrite (22 ml) and a solution of 3-fluoro-4-methylaniline (20.0 g) in chloroform were added simultaneously. The mixture was then stirred at room temperature for 2 hours. The mixture was washed with water, hydrochloric acid (2M), water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness to give 2-fluoro-4-(methylsulphenyl)toluene (25.37 g) as a red oil which was not further purified.

Workup

  1. washThe mixture was washed with water, hydrochloric acid (2M), water
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-71c25232191642829750fad44fcb71ff
Source dataset
uspto-grants-1998_09
Patent number
US05804532

Linked notes

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