2-Bromopropane → Methyl 4-isopropoxy-3-(methoxymethyl)benzoate

Participants

Reaction Conditions

Reaction Steps

Methyl 4-hydroxy-3-(methoxymethyl)benzoate (9.50 g; 48.42 mmol; 1 eq.) was dissolved in DMF (142.50 mL). Then K2CO3 (26.77 g; 193.68 mmol; 4 eq.) and 2-bromopropane (18.18 mL; 193.68 mmol; 4 eq.) were added to the reaction mixture. It was heated to 90° C. for 3 hours. The reaction mixture was cooled to RT and diluted with EtOAc. It was washed with water (3×), brine, dried over MgSO4 and concentrated affording the title compound as a yellow oil (11.35 g, 98%). 1H NMR (DMSO-d6, 300 MHz) δ 7.95-7.84 (m, 2H), 7.13-7.11 (d, J=8.63 Hz, 1H), 4.81-4.69 (sept, J=6.07 Hz, 1H), 4.39 (s, 2H), 3.81 (s, 3H), 3.36 (s, 3H), 1.31-1.29 (d, J=6.01 Hz, 6H). LC/MS (Method B): 239.2 (M+H)+. HPLC (Method A) Rt 4.25 min (Purity: 95.8%).

Provenance & Evidence