3-Bromocyclohexene was used in the synthesis of N-tert-butoxycarbonyl-O-cyclohexyl-L-tyrosine. It was also used in the synthesis of enantiopure cyclohexitols such as muco-quercitol, D-chiro-inocitol and allo-inocitol.
The general procedure for the synthesis of 3-bromocyclohexene from cyclohexene was as follows: cyclohexene (8.2 g, 0.1 mol) and N-bromosuccinimide (NBS, 21.4 g, 0.12 mol) were dissolved in carbon tetrachloride (CCl4, 100 mL) at room temperature, and azobisisobutyronitrile (AIBN, 3.3 g, 20 mmol) was subsequently added as initiator. . The reaction mixture was heated to reflux for 3 hours. Upon completion of the reaction, the reaction mixture was washed sequentially with sodium sulfite (Na2SO3) solution, saturated sodium bicarbonate (NaHCO3) solution and brine to remove unreacted reagents and by-products. The organic layer was dried with anhydrous sodium sulfate (Na2SO4) and subsequently concentrated under reduced pressure to afford the crude product 3-bromocyclohexene (8.5 g, 53% yield). The product did not require further purification and could be used directly in the subsequent reaction.
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