Imidazole → 1-Fluoro-4-((4-iodobut-2-enyloxy)methyl)-2-methylbenzene

Temperature

0 °C

To a solution of triphenylphosphine (2.6 g, 9.9 mmol) in anhydrous 40 mL DCM was added imidazole (1.4 mg, 20.4 mmol) and iodine (2.5 mg, 9.9 mmol) at 0° C. The reaction mixture was stirred for 30 min at 0° C. and then 4-(4-Fluoro-3-methylbenzyloxy)but-2-en-1-ol (1.3 g, 6.2 mmol) in 10 mL DCM was added to the mixture. The resulting mixture was stirred at 0° C. for 2 h and the temperature was slowly raised to room temp over a period of 2 h. 20 mL of 10% sodium thiosulfate was added and extracted with more DCM (3×30 mL). The combined DCM layer was washed with brine (2×30 mL) and dried over sodium sulfate. Evaporation of solvent left the crude product as an oil from which the product was isolated by Flash column chromatography eluting with 0% to 10% ethyl acetate/hexane to give the title compound, 1.5 g, as a light yellow oil.

1. stirringThe resulting mixture was stirred at 0° C. for 2 h
2. temperaturethe temperature was slowly raised to room temp over a period of 2 h
3. extractionextracted with more DCM (3×30 mL)
4. washThe combined DCM layer was washed with brine (2×30 mL)
5. dry with materialdried over sodium sulfate
6. customEvaporation of solvent
7. waitleft the crude product as an oil from which the product
8. customwas isolated by Flash column chromatography
9. washeluting with 0% to 10% ethyl acetate/hexane

ORD record

ord-bc79be4db39646f3a60a62890af4a380

Source dataset

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07879911B2