Trimethyl borate → 2,8-Diphenyldibenzothiophen-4-boronic acid

Participants

Reaction Conditions

Reaction Steps

2,8-diphenyldibenzo[b,d]thiophene (6.0) was dissolved in anhydrous tetrahydrofuran (80 mL) under nitrogen atmosphere and the solution was then cooled to −78° C. 20.0 mL of n-butyl lithium (1.6 M solution) was added dropwise into the reaction mixture and continuously stirred to equilibrate to room temperature. The reaction mixture was then cool to −60° C. and trimethyborate (5.67 mL) was added and the reaction was allowed to stir overnight. The reaction was then quenched with 20% aqueous hydrochloric acid, and extracted the organic layer with ethyl acetate; ethyl acetate layer was then washed thoroughly with water and dried over anhydrous sodium sulfate, and was evaporated to dryness to yield 4.5 g of 2,8-diphenyldibenzo[b,d]thiophene-4-boronic acid.

Provenance & Evidence