Water → 3-Fluoro-4-methylphenyl methyl sulfide

HRID 2380198

Reaction equation

HRID 2380198 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[CH3:9])N.[CH3:10][S:11]SC.N(OC(C)(C)C)=O.O>ClCCCl>[F:1][C:2]1[CH:3]=[C:4]([S:11][CH3:10])[CH:6]=[CH:7][C:8]=1[CH3:9]

Participants

6

Reactant 4

HCID 962WaterHCID 99573-Fluoro-4-methylaniline2×HCID 10906Tert-Butyl nitrite2×HCID 12232Dimethyl Disulfide

Product 1

HCID 534144923-Fluoro-4-methylphenyl methyl sulfideYield 525.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

A mixture of 3-fluoro-4-methylaniline (25 g), dimethyl disulphide (375 g) and t-butyl nitrite (30 ml) in 1,2-dichloroethane was warmed to start the reaction. A solution of 3-fluoro-4-methylaniline (225 g) in 1,2-dichloroethane was added dropwise, simultaneously with t-butyl nitrite (241 ml) at such a rate as to maintain the temperature below 60° C. The mixture was stirred for 2 hours, then water was added. The organic layer was washed with water, hydrochloric acid, dried (anhydrous magnesium sulphate) and filtered. The filtrate was evaporated to dryness and the residue was distilled to give 2-fluoro-4-(methylsulphenyl)toluene (164 g) as a yellow oil; NMR (acetone-d6); 2.2 (3H,d), 2.5 (3H,s), 7.05 (3H,m).

Workup

  1. temperaturewas warmed
  2. customthe reaction
  3. temperatureto maintain the temperature below 60° C
  4. washThe organic layer was washed with water, hydrochloric acid
  5. dry with materialdried (anhydrous magnesium sulphate)
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness
  8. distillationthe residue was distilled

Sources & evidence

ORD record
ord-e634bd928cd6473b8d99d6687553a94c
Source dataset
uspto-grants-1994_11
Patent number
US05366957

Linked notes

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