Dimethyl Sulfate → 1-Bromo-3,5-di-tert-butyl-2-methoxybenzene

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Reaction Steps

A procedure analogous the synthesis of 1-methoxymethylether-2,4-di-t-butyl-6-bromobenzene was employed. The MOMCl was replaced with Me2SO4 as alkylating agent. Starting from 20 g of 2,4-di-t-butyl-phenol, 26.8 g (92% yield over two steps) of 1-methoxy-2,4-di-t-butyl-6-bromobenzene were obtained. 1H NMR (300 MHz, CDCl3) δ: 1.30 (s, 9H, C(CH3)3), 1.41 (s, 9H, C(CH3)3), 3.92 (s, 3H, OCH3), 7.29 (d, 2H, aryl-H, 4J=2.3 Hz), 7.42 (d, 2H, aryl-H, 4J=2.3 Hz). 13C NMR (75 MHz, CDCl3) δ: 31.1 (C(CH3)3), 31.6 (C(CH3)3), 34.8 (C(CH3)3), 35.9 (C(CH3)3), 61.5 (OCH3), 117.8, 123.8, 129.0, 144.2, 147.4, 154.3 (aryl). GC-MS: M+=298.

Provenance & Evidence