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Stage #1: With n-butyllithium In tetrahydrofuran at -78℃; for 1 h; Stage #2: With boric acid tributyl ester In tetrahydrofuran at -78 - 0℃; Stage #3: With hydrogenchloride In tetrahydrofuran; water at 0℃;
A solution of 4-bromo-3-ethyl anisole (94 g, 0.437 mol) in THF (900 ml) was cooled to -78° C. n-Butyl lithium (249 ml, 0.55 mol) was added dropwise at the same temperature. Stirring was continued for 1 hr at -78°0 C. Tri-n-butyl borate (177 ml, 0.655 mol) was added slowly at -78° C. The cooling bath was removed, the reaction mixture was allowed to warm to 0° C. and was quenched with 1.5 N hydrochloric acid at 0° C. The organic layer was separated. The aqueous layer was extracted with ethylacetate and the combined organic layers were washed with brine and concentrated. The residue obtained was stirred in pet-ether for 30 min. The solid obtained was filtered and dried under vacuum. Yield: 65 g, 82percent, as a white solid.
Reference：
[1] Patent: US2006/4222, 2006, A1, . Location in patent: Page/Page column 1-6
[2] Journal of Medicinal Chemistry, 2009, vol. 52, # 23, p. 7788 - 7799
A solution of 4-bromo-3-ethyl anisole (94 g, 0.437 mol) in THF (900 ml) was cooled to -78 C. n-Butyl lithium (249 ml, 0.55 mol) was added dropwise at the same temperature. Stirring was continued for 1 hr at -780 C. Tri-n-butyl borate (177 ml, 0.655 mol) was added slowly at -78 C. The cooling bath was removed, the reaction mixture was allowed to warm to 0 C. and was quenched with 1.5 N hydrochloric acid at 0 C. The organic layer was separated. The aqueous layer was extracted with ethylacetate and the combined organic layers were washed with brine and concentrated. The residue obtained was stirred in pet-ether for 30 min. The solid obtained was filtered and dried under vacuum. Yield: 65 g, 82%, as a white solid.
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