6-Bromo-2-methyl-4-nitrophenol

Methylphenol in ethanolic solution treated with ferric nitrate nonahydrate (1 equiv.) and heated briefly for 30 sec. afforded an 83% yield of 4-methyl-2-nitrophenol. Under similar conditions 4-chlorophenol gave 4-chloro-2-nitrophenol (88%), 4-bromophenol gave 4-bromo-2-nitrophenol (64%) and 2-chlorophenol, a mixture of 2-chloro-4-nitrophenol (56%) and 2-chk>ro-6-nitrophenol (35%). Aluminium, chromium and copper(ll) nitrates were also used (ref.63). 

Cl3H2 7BrMg03, Tris(tetrahydrofuran)bromo(methyl)magnesium, 40B, 1103 Cl4H11KN2O5, Potassium o-nitrophenolate-isonitrosoacetophenone, 37B, 404... 

Bromo-4-methyl-6-nitrophenol (2-Bromo-6-nitro-p-cresol) 69, yel 128 IIO-II ... 

Furoannulated carbazole alkaloids represent a relatively new class of natural products which have been isolated from terrestrial plants [121,122]. The number of members of this family known to date is rather limited. Furoclausine-A (61) along with furoclausine-B was isolated first by Wu and co-workers from the root bark of C. excavata [122]. We have developed an efficient and convergent access to furo [3,2-a]carbazoles via our iron-mediated arylamine cyclization [123, 124]. Retro-synthetic analysis of furoclausine-A (61) suggests 1-methoxycyclohexa-1,4-diene (48) and the arylamine 62 as building blocks (Scheme 16). The latter was obtained by alkylation of 2-methyl-5-nitrophenol (63) with 2-bromo-1,1-diethoxyethane... 

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