Methanol → Methyl 3-bromo-5-ethylbenzoate
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH2:11][CH3:12])[CH:10]=1)[C:5]([OH:7])=[O:6].O=S(Cl)Cl.[CH3:17]O>>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([CH2:11][CH3:12])[CH:10]=1)[C:5]([O:7][CH3:17])=[O:6]Participants
4
Conditions
- Temperature
- 0 °C
Procedure
The compound 3-bromo-5-ethylbenzoic acid (0.95 g, 4.14 mmol) was dissolved in MeOH (50 mL), reaction mixture was cooled to 0° C. and SOCl2 (0.5 mL) was added. The reaction mixture was allowed to stir at room temperature for 10 h. The reaction mixture was concentrated under reduced pressure and diluted with CH2Cl2. The organic layer was washed with 10% NaHCO3 solution, water and brine. The organic phase was dried over anhydrous sodium sulfate and solvent was removed under reduced pressure. Methyl 3-bromo-5-ethylbenzoate (0.92 g, yield 92%) was isolated as colorless liquid and carried through without further purification. 1H NMR (300 MHz, CDCl3) δ 7.99 (t, J=1.6 Hz, 1H), 7.81 (d, J=1.4 Hz, 1H), 7.54 (t, J=1.6 Hz, 1H), 3.92 (s, 3H), 2.69 (q, J=7.6 Hz, 2H), 1.26 (t, J=7.6 Hz, 3H).