Benzene, 1-bromo-3-(trifluoromethyl)- → 2,2-Difluoro-1-(3-trifluoromethyl-phenyl)-1,2,3,6,7,8,9,10-octahydro-8-aza-cyclohepta[e]indene

Participants

Reaction Steps

Example 18 was prepared in a similar fashion to Example 14, except (3-(trifluoromethyl)phenyl)magnesium chloride (prepared from 3-bromobenzotrifluoride (1 eq) in THF, followed by addition of isopropyl magnesium chloride (2M in THF, 1 eq) at room temperature and stirring for 16 hours was used instead of phenylmagnesium bromide (example 14, step (c)) 1H NMR (300 MHz, CDCl3) δ 7.55-7.53 (m, 1H); 7.42 (t, J=7.8 Hz, 1H); 7.29 (bs, 1H); 7.20-7.17 (m, 1H); 7.13-7.07 (m, 2H); 4.70 (d, J=19.2, 1H); 3.51-3.36 (m, 2H); 3.01-2.84 (m, 4H); 2.74-2.61 (m, 2H); 2.54-2.49 (m, 2H); 2.01 (bs, 1H); MS: ESI (positive): 368 (M+1).

Provenance & Evidence