Triethoxychlorosilane → 2-(Triethoxysilyl)thianthrene

Participants

Reaction Steps

A 3-neck 3 L flask was filled with magnesium turnings (20 g), THF (650 g) and chlorotriethoxysilane (146 g), and heated to reflux. 2-Bromothianthrene from Example 3A was added to the flask in small portions. Grignard started instantly. The reaction was allowed to cool for 1 hour, after which magnesium salts were precipitated with hexanes (500 mL). The solution was filtered, followed by evaporation of volatiles by rotary evaporator. The material was distilled twice at 190 . . . 200° C./<1 mbar, giving colorless 2-(triethoxysilyl)thianthrene (125.9 g, 69.8% overall yield based on thianthrene, purity >99% by GC/MS).

Provenance & Evidence