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Exercício de Química Sintética e Organica Mista (649)
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Reduce nitro group to amine: Replace amino group by fluorine: (e) Bromination of the starting material will introduce the bromine substituent at the correct position, that is, ortho to the tert-butyl group. The desired product will be obtained if the nitro group can be removed. This is achieved by its conversion to the corresponding amine, followed by reductive deamination. ( f ) The proper orientation of the chlorine substituent can be achieved only if it is introduced after the nitro group is reduced. The correct sequence of reactions to carry out this synthesis is shown. C(CH3)3 Cl NO2 C(CH3)3 NH2 Cl C(CH3)3 NH2 C(CH3)3 C(CH3)3 Br NO2 2-Bromo-1-tert- butyl-4-nitrobenzene C(CH3)3 Br NH2 3-Bromo-4-tert- butylaniline C(CH3)3 Br o-Bromo-tert- butylbenzene H2, Ni (or other appropriate reducing agent) 1. NaNO2, H � 2. H3PO2 C(CH3)3 NO2 p-tert-Butyl- nitrobenzene C(CH3)3 Br NO2 2-Bromo-1-tert- butyl-4-nitrobenzene Br2, Fe Br NH2 CH3 4-Bromo-3-methyl- 1-naphthylamine Br F CH3 1-Bromo-4-fluoro-2- methylnaphthalene (64%) 1. NaNO2, HCl, H2O, 0–5�C 2. HBF4 3. heat Br NO2 CH3 1-Bromo-2-methyl- 4-nitronaphthalene Br NH2 CH3 4-Bromo-3-methyl- 1-naphthylamine 1. Fe, HCl 2. HO� 644 AMINES
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