2-Methyl-4-methoxycarbonylphenylboronic acid, pinacol ester → 4-(Bicyclo[3.2.1]oct-2-en-2-yl)-3-methyl-benzoic acid methyl ester
Reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7](B2OC(C)(C)C(C)(C)O2)=[C:6]([CH3:19])[CH:5]=1.FC(F)(F)S(O[C:27]1[CH:28]2[CH2:34][CH:31]([CH2:32][CH:33]=1)[CH2:30][CH2:29]2)(=O)=O>>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][C:7]([C:27]2[CH:28]3[CH2:34][CH:31]([CH2:32][CH:33]=2)[CH2:30][CH2:29]3)=[C:6]([CH3:19])[CH:5]=1Participants
3
Procedure
3-Methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester of Example 28, Step A (0.300 g, 1.09 mmol) and bicyclo[3.2.1]oct-2-en-2-yl trifluoromethanesulfonate (0.336 g, 1.31 mmol) were reacted in the manner of Example 1, Step F. Purification by flash column chromatography on silica gel, eluting with 5% ethyl acetate in hexane, afforded the title compound (0.161 g) as a light yellow oil.