反应 #1188831
相关文献 (1)
openreactiondata ↗doi:10.6084/m9.figshare.5104873.v1; patent:US08933018B2
反应条件: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.
实验步骤: To a 2.5 M solution of n-BuLi in hexane (27.81 mL, 69.53 mmol) in dry THF (30 mL), cooled to −78° C. and under an Argon atmosphere was added a solution of (2-bromo-6-(trifluoromethyl)phenyl)methanol (CXXIX) (5.49 g, 23.16 mmol) in dry THF (30 mL) dropwise very slowly. The reaction mixture was stirred at −78° C. for 2 h before adding trimethyl borate (3.88 mL, 34.76 mmol). The reaction mixture was stirred at −78° C. for an additional 30 min, and then allowed to warm up slowly to room temperature and stirred overnight. The reaction was then cooled to 0° C. and slowly quenched with 2 M HCl and stirred for 2.5 h at room temperature. The reaction mixture was extracted with EtOAc and the organic layer was dried over anhydrous MgSO4. The solvent was removed under reduced pressure and the crude product was purified by silica gel chromatography using (100:1 DCM/MeOH) to give 4-(trifluoromethyl)benzo[c][1,2]oxaborol-1(3H)-ol (CXXX) as an orange oil (1.17 g, 5.79 mmol, 25% yield). ESIMS found for C8H6BF3O2 m/z 201.4 (M−H). The reaction mixture was stirred at −78° C. for an additional 30 min to warm up slowly to room temperature stirred overnight The reaction was then cooled to 0° C. slowly quenched with 2 M HCl stirred for 2.5 h at room temperature The reaction mixture was extracted with EtOAc the organic layer was dried over anhydrous MgSO4 The solvent was removed under reduced pressure the crude product was purified by silica gel chromatography
来源 ID: ord-59e017cc326b4bbc93780fb83a4cc6a6