Imidazole → (3-Iodo-1-trifluoromethylpropyl)-benzene

To a stirred solution of triphenylphosphine (3.93 g) and imidazole (1.02 g) in dichloromethane (20 ml) under an argon atmosphere was added slowly iodine (3.81 g) and rac-4,4,4-trifluoro-3-phenyl-butan-1-ol (2.04 g, CAS 65948-16-5). The mixture was stirred for 2 hours at room temperature, then dichloromethane (50 ml) was added and mixture was extracted with saturated sodium thiosulfate solution (50 ml) and hydrochloric acid (1N, 25 ml). The organic layer was dried over MgSO4 and evaporated. The residue was suspended in ether and filtered to remove insoluble triphenylphosphine oxide. The ether was evaporated and the residue was purified by column chromatography (SiO2, heptane/EtOAc=9:1) to yield a light yellow liquid, (1.99 g, 63%).

1. extractionmixture was extracted with saturated sodium thiosulfate solution (50 ml) and hydrochloric acid (1N, 25 ml)
2. dry with materialThe organic layer was dried over MgSO4
3. customevaporated
4. filtrationfiltered
5. customto remove insoluble triphenylphosphine oxide
6. customThe ether was evaporated
7. customthe residue was purified by column chromatography (SiO2, heptane/EtOAc=9:1)
8. customto yield a light yellow liquid, (1.99 g, 63%)

ORD record

ord-0352fb3f7b2549969cdbf1b00efaa353

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08729113B2