2-Bromopropane → 4-Isopropoxy-2-methyl-1-nitrobenzene

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Reaction Steps

This compound was prepared in a similar manner to that for 404b except that 2-bromopropane was deployed for the alkyl ether adduct and chromatography utilized a 0% to 15% gradient for elution to yield a yellow oil (1.87 g, 98%): TLC Rf 0.68 (20% EtOAc/hexanes). 1H NMR (600 MHz, CDCl3) δ 8.08-8.07 (d, 1H, J=8.82 Hz), 6.77-6.75 (m, 2H), 4.66-4.62 (sep, 1H, J=6.06 Hz), 2.62 (s, 3H), 1.38-1.37 (d, 6H, J=6.12 Hz). 13C NMR (150 MHz, CDCl3) δ 162.6, 141.7, 137.1, 127.6, 118.9, 112.8, 70.6, 21.84, 21.78. Elemental analysis calculated for C10H13NO3.0.06 hexanes: C, 62.10; H, 6.96; N, 6.99. Found: C, 62.45; H, 6.69; N, 7.09.

Provenance & Evidence