Aniline, formation Bromobenzene

A series of N-alkylmorpholines gives secondary and tertiary aniline derivatives 213 and 214 when treated with bromobenzene and sodium amide.108 A route for formation of these products via the ylid 211 is outlined in Scheme 19, in which the formation of 211 is similar to that of 16 in Scheme 2 and the step 212 - 213 is similar to the decomposition of 33 in Scheme 5. The final... 

It may be remembered (Chapter 7, Scheme 7.13) that treatment of aryl halides, such as bromobenzene (CeHsBr), with liquid ammonia (NH3(i)) (Equation 10.22) results in the formation of benzyne (C6H4), and the capture of the latter by ammonia (NH3) produces aminobenzene (aniline). 

---