Tetrahydrofuran → Methyl 4-bromo-3-((methylthio)methyl)benzoate

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Reaction Steps

To a solution of methyl 4-bromo-3-(bromomethyl)benzoate, which preparation is described above, under Intermediate 28, Step 1, (2 g; 6.49 mmol; 1 eq.) in CH3CN (10 mL) and THF (10 mL) was added sodium thiomethoxide (0.50 g; 7.14 mmol; 1.10 eq.) and the mixture was stirred at reflux for 1 hour and at RT overnight. After concentration under vacuum, the mixture was partitioned between EtOAc and water. The organic layer was washed with NaCl sat. solution, dried over magnesium sulfate, filtered off and dried under vacuum to give the title compound as a yellow oil (1.7 g, 94%). 1H NMR (CDCl3) δ 7.99 (d, J=2.3 Hz, 1H), 7.77 (dd, J=8.3, 2.1 Hz, 1H), 7.65 (d, J=8.3 Hz, 1H), 3.92 (s, 3H), 3.83 (s, 2H), 2.06 (s, 3H). HPLC (Method A) Rt 4.31 min (Purity: 87.4%).

Provenance & Evidence