Methyl iodide → 2-(4-Bromo-2-fluorophenyl)-2-methylpropyl methyl ether

Temperature

0 °C

To a DMF (4 ml) solution of 2-(4-bromo-2-fluorophenyl)-2-methylpropan-1-ol (199 mg, 0.8 mmol, WO2004074270A2) was added 60% sodium hydride (35 mg, 0.88 mmol) at 0° C. and the mixture was stirred at 0° C. for 15 minutes followed by additional stirring for 1 hour at room temperature. After the mixture was cooled to 0° C., methyliodide (342 mg, 2.4 mmol) was added and the mixture was stirred for 30 minutes at 0° C. followed by additional stirring for 16 hours at room temperature. Then, the reaction was quenched with water and the whole was extracted with EtOAc, which was dried over sodium sulfate. Then, filtration, evaporation and purification by silica gel column chromatography, eluting with hexane/EtOAc (20:1), gave the title compound (174 mg, 83% yield) as a colorless oil.

1. stirringby additional stirring for 1 hour at room temperature
2. temperatureAfter the mixture was cooled to 0° C.
3. stirringthe mixture was stirred for 30 minutes at 0° C.
4. stirringby additional stirring for 16 hours at room temperature
5. customThen, the reaction was quenched with water
6. extractionthe whole was extracted with EtOAc, which
7. dry with materialwas dried over sodium sulfate
8. filtrationThen, filtration, evaporation and purification by silica gel column chromatography
9. washeluting with hexane/EtOAc (20:1)

ORD record

ord-5bba1f4c8f314a07b9a9990ba8afbf87

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07622589B2