4-Chlorotoluene → [4-(1,3,4-oxadiazol-2-yl)phenyl]boronic Acid

Participants

Reaction Conditions

Reaction Steps

Lithium granules (8.2 g) and tetrahydrofuran (670 g) were charged to a reactor under an argon atmosphere and the mixture cooled to −35° C. 4-Chlorotoluene (74.3 g) was added at −35° C. and the mixture was held at this temperature for 6 hours. The resultant solution was added to a suspension of 2-(4-bromophenyl)-1,3,4-oxadiazole (124.4 g) in tetrahydrofuran (800 g) at −65° C. After 30 mins a solution of n-hexyllithium (33% w/w in hexanes) (240 ml) was then added at −65° C. After a further 30 min triisopropylborate (230.8 g) was then added maintaining the reaction mixture at −65° C. The reaction mixture was allowed to warm to −35° C. and drowned out into a solution of acetic acid (91.5 g) in water (688 g). The resultant solid was isolated, washed with THF and water, and dried to yield the title compound (92.2 g, 88%).

Provenance & Evidence