Water → 3-Fluoro-4-methylphenyl methyl sulfide

HRID 21451

Reaction equation

HRID 21451 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-9b753ec268a24204821843de40f5cfd5
Source dataset
uspto-grants-1995_06
Patent number
US05424276

Linked notes

Loading…