Iodoethane → 2-Bromo-1-ethoxy-4-methylbenzene

To a solution of 2-bromo-4-methyl-phenol (1 g, 5.346 mmol) in acetone (10 mL) were added potassium carbonate (740 mg, 5.346 mmol) and ethyl iodide (868 μL, 10.69 mmol). The reaction mixture was heated at gentle reflux for 12 h. The solvent was removed to give a white paste. It was then taken in diethyl ether (5 mL) and water (2 mL). The product was extracted with diethyl ether (2×20 mL). The organic layers were washed with brine (1×5 mL) and dried over anhydrous sodium sulfate. The solid was then filtered off, and the filtrate was concentrated in vacuo. Purification of the crude residue by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel) eluting with 5% ethyl acetate in hexanes yielded 2-bromo-1-ethoxy-4-methyl-benzene (940 mg, 82%).

1. temperatureThe reaction mixture was heated
2. temperatureat gentle reflux for 12 h
3. customThe solvent was removed
4. customto give a white paste
5. extractionThe product was extracted with diethyl ether (2×20 mL)
6. washThe organic layers were washed with brine (1×5 mL)
7. dry with materialdried over anhydrous sodium sulfate
8. filtrationThe solid was then filtered off
9. concentrationthe filtrate was concentrated in vacuo
10. customPurification of the crude residue by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel)
11. washeluting with 5% ethyl acetate in hexanes

ORD record

ord-10ec418fb12d4a04af9d8955d7c08c4e

Source dataset

uspto-grants-2003_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06617346B1