Boron tribromide → Methyl 4-hydroxy-2,2-dimethyl-2,3-dihydro-1-benzofuran-6-carboxylate

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Reaction Conditions

Reaction Steps

To the mixture of 4-methoxy-2,2-dimethyl-2,3-dihydro-benzofuran-6-carboxylic acid methyl ester and 6-methoxy-2,2-dimethyl-2,3-dihydro-benzofuran-4-carboxylic acid methyl ester (3d) (1.74 g, 7.36 mmol) in CH2Cl2 (10 mL) at 0° C. was added BBr3 (22.0 mL, 22 mmol, 1.0 M solution in CH2Cl2). The reaction mixture was stirred at 0° C. for 6 hr, quenched with H2O (100 mL), extracted with CH2Cl2(2×100 mL), dried over MgSO4, and concentrated in vacuo. The residue was purified by flash column chromatography eluting with 10% EtOAc in hexanes to give an pale yellow solid (171 mg, 10% yield). 1H NMR (400 MHz, CDCl3) δ 7.15 (s, 1 H) 6.99 (s, 1 H) 5.87 (s, 1 H) 3.89 (s, 3 H) 3.00 (s, 2 H) 1.50 (s, 6 H); LCMS for C12H14O4 m/z 223.0 (M+H)+.

Provenance & Evidence