Réaction #49729

Équation de réaction

water

3-fluoro-4-methylaniline

dimethyl disulphide

t-butyl nitrite

3-fluoro-4-methylaniline

t-butyl nitrite

→

2-fluoro-4-(methylsulphenyl)toluene

Solvants

1,2-dichloroethane

1,2-dichloroethane

Conditions de réaction

Traitement

1. 1
   Températurewas warmed
2. 2
   Autrethe reaction
3. 3
   Températureto maintain the temperature below 60° C
4. 4
   LavageThe organic layer was washed with water, hydrochloric acid
5. 5
   Séchagedried (anhydrous magnesium sulphate)
6. 6
   Filtrationfiltered
7. 7
   AutreThe filtrate was evaporated to dryness
8. 8
   workup.DISTILLATIONthe residue was distilled

Mode opératoire

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).

Source