Trimethyl borate → Boronic acid, B-[3-(hydroxymethyl)-2-methylphenyl]-

Participants

Reaction Steps

Butyllithium (2.5 M, 4 mL, 10 mmol), 3-iodo-4-methyl-benzyl alcohol (1 g, 4 mmol), and trimethylborate (6 mL, 53 mmol) were reacted as in Example 5: step b. Aqueous workup and purification by SiO2 flash chromatography (40–50% EtOAc in hexanes) yielded the title compound (180 mg, 27%). The title compound exists as a mixture of boronic acids and anhydrides in CDCl3, therefore the reported NMR signals represent pairs or groups of related signals. 1H-NMR (CDCl3): δ 7.06–7.30 (m, 3H), 4.56 (s, 3H), 4.16 (br s, 1H), 2.32 (s, 3H).

Provenance & Evidence