Trimethyl borate → 4-(1,3-Dioxolan-2-yl)-3-(trifluoromethyl)phenylboronic acid
반응식
I[C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[O:12][CH2:11][CH2:10][O:9]2)=[C:4]([C:13]([F:16])([F:15])[F:14])[CH:3]=1.C([Mg]Cl)(C)C.[B:22](OC)([O:25]C)[O:23]C.C(OB1OC(C)(C)C(C)(C)O1)(C)C>>[O:9]1[CH2:10][CH2:11][O:12][CH:8]1[C:5]1[CH:6]=[CH:7][C:2]([B:22]([OH:25])[OH:23])=[CH:3][C:4]=1[C:13]([F:16])([F:15])[F:14]참가 물질
5
실험 절차
The title compound was prepared from 2-[4-iodo-2-(trifluoromethyl)phenyl]-1,3-dioxolane (Example I-IX-7) according to the procedure described for Example V-18, with the following exceptions: the aryl iodide and i-PrMgCl were aged 45 min before introduction of the electrophile (instead of 30 min); trimethyl borate was used as the electrophile (instead of 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane); the dried organic extracts were concentrated to dryness and triturated with Et2O/hexanes (instead of flash chromatography). White solid. LC/MS (method A) 2.22 min, m/z 417 ({2[M-gylcol]-H2O}—H, 23%), 217 ([M-glycol]-H, 57%), 189 (100%, −ve ion).