Methane → (2-Chloro-6-fluorophenyl)-P-tolyl-amine

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-bromo-1-chloro-3-fluorobenzene (32 g, 153 mmol), p-toluidine (16.4 g, 153 mmol), sodium tert.butylate (27.5 g, 286 mmol), (±)-BINAP [2,2′-Bis-(diphenylphosphino)-1,1′-binaphthalin, 0.66 g, 1.1 mmol) and toluene (250 ml) is stirred under nitrogen for about 30 minutes. After the addition of Palladium-bis-(dibenzylidenaceton) (0.8 g, 1 mmol), the mixture is heated to 110° C. (slight reflux) for 14-20 hours. The mixture is then cooled to 30° C., water (60 ml), concentrated hydrochloric acid (60 ml) as well as charcoal and cellite (5 g each) are added and stirring is continued for an hour. The mixture is filtered and the filtrate is separated into the phases. The organic phase is washed with water (3 times, 70 ml each) and concentrated in vacuo to obtain 37.2 g of crude (2′-chloro-6′-fluorophenyl)-(4-methylphenyl)-amine. The product can be used in the next step (Step 1.2) as such; alternatively in can be kugelrohrdistilled in vacuo.

Provenance & Evidence