Reagents and conditions:
(a) 16, Pd(PPh3)4, Na2CO3, PhCH3, H2O, 65 °C, 24
h, 48%;
(b) o-anisylmagnesium bromide, THF, Ni(acac)2, dppe, rt, 24 h, 77%; (c) Na, EtOH, reflux, 3 h, 38% (30a), 38% (30b); (d) Br2, 1:1 CH3COOH/1,4-dioxane, 0 °C to rt, 18 h, 66% (8a), 87% (8b).