Water → HCID 12559766, compound

Temperature

65 °C

To a stirred solution of 1-bromo-4-fluoro-2-methoxybenzene (10.0 g) in DMF (100 mL) was added sodium methanethiolate (4.44 g). The mixture was stirred at 65° C. for 2 h. The mixture was cooled to 0° C. and methyl iodide (4.55 mL) was added. The mixture was stirred at room temperature for 1 h and further sodium methanethiolate (4.44 g) was added. The mixture was stirred at 65° C. for 1 h. The mixture was cooled to 0° C. and methyl iodide (4.55 mL) was added. The mixture was stirred at room temperature for 1 h. Water was added and the mixture was extracted with ethyl acetate. The organic phase was washed with saturated sodium chloride solution, dried (sodium sulfate) and the solvent was removed in vacuum. Silica gel chromatography gave 6.2 g of the title compound as a 2:1 mixture with the starting material. The mixture was used for the next step without purification.

1. temperatureThe mixture was cooled to 0° C.
2. stirringThe mixture was stirred at room temperature for 1 h
3. stirringThe mixture was stirred at 65° C. for 1 h
4. temperatureThe mixture was cooled to 0° C.
5. stirringThe mixture was stirred at room temperature for 1 h
6. extractionthe mixture was extracted with ethyl acetate
7. washThe organic phase was washed with saturated sodium chloride solution
8. dry with materialdried (sodium sulfate)
9. customthe solvent was removed in vacuum

ORD record

ord-50d0aa0209674751a7e7b962ed2531d6

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09388177B2