Isopropyl iodide → Methyl 3-bromo-4-isopropoxybenzoate

Participants

Reaction Conditions

Reaction Steps

A mixture of 4.6 g (19.9 mmol) of methyl 3-bromo-4-hydroxybenzoate (from Step A), 2.2 mL (21.9 mmol) of 2-iodopropane and 5.5 g (39.8 mmol) of potassium carbonate in 10 mL of DMF was stirred at 65° C. for 3 h. The mixture was diluted with 20 mL of EtOAc and washed with sat'd NaCl, H2O (3×), and sat'd NaCl. The organic layer was dried over MgSO4 and concentrated. Chromatography on a Biotage 40M cartridge using 24:1 v/v hexanes/EtOAc gave 4.3 g of the title compound: 1H NMR (500 MHz, CDCl3) δ 1.44 (d, J=6.2, 6H), 3.91 (s, 3H), 4.71-4.79 (m, 1H), 6.99 (d, J=8.9, 1H), 8.18 (dd, J=2.2, 8.8, 1H), 8.24 (d, J=2.1, 1H).

Provenance & Evidence