4-Chloro-alpha,alpha,alpha-trifluoro-3-nitrotoluene → 2-Nitro-1-(2-phenylchroman-6-yloxy)-4-trifluoromethylbenzene

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Reaction Steps

2-Nitro-1-(2-phenylchroman-6-yloxy)-4-trifluoromethylbenzene was prepared as described for 2-nitro-1-(2-phenylchroman-6-yloxy)-benzene in Example 29(a) except that 6-hydroxyflavane (0.339 g) was used in 7 ml of dry DMSO under nitrogen. Also KI (0.374 g) and KOH (0.168 g) and 4-chloro-3-nitro-1-trifluoromethylbenzene (0.24 ml) were added in similar manner. Product was purified by column chromatography (CH2Cl2:n-heptane/60:40). 1H-NMR (300 MHz; d6-DMSO): δ 8.44 (d, 1H, J=2.1 Hz), 7.99 (dd, 1H, J=9.0 Hz; J=2.2 Hz), 7.51-7.29 (m, 5H), 7.15 (d, 1H, J=8.7 Hz), 7.09-6.91 (m, 3H), 5.15 (dd, 1H, J=10.1 Hz; J=2.3 Hz), 3.08-2.90 (m, 1H), 2.83-2.68 (m, 1H), 2.25-2.11 (m, 1H), 2.09-1.91 (m, 1H).

Provenance & Evidence