Imidazole → (R)-(1-Iodobutan-2-yl)benzene

To a solution of triphenylphosphine (15.4 g, 59 mmol) and imidazole (3.99 g, 59 mmol) in dichloromethane (150 ml) at room temperature was added portionwise iodine (14.9 g, 50 mmol) at such a rate that the temperature of the reaction mixture did not rise above 30° C. To the mixture was then added a solution of (R)-2-phenyl-butan-1-ol (7.34 g, 41 mmol, CAS 16460-75-6) in dichloromethane (50 ml) and the mixture was then stirred at room temperature overnight. The mixture was then concentrated in vacuo and the residue was resuspended in ether and the resulting crystals collected by filtration. The filtrate was concentrated in vacuo and the residue was triturated in heptane. The resulting crystals were removed by filtration and the filtrate was concentrated in vacuo. The residue was purified by column chromatography (SiO2, heptane/EtOAc) to yield a colourless oil, (6.38 g, 60%).

1. customdid not rise above 30° C
2. concentrationThe mixture was then concentrated in vacuo
3. filtrationthe resulting crystals collected by filtration
4. concentrationThe filtrate was concentrated in vacuo
5. customthe residue was triturated in heptane
6. customThe resulting crystals were removed by filtration
7. concentrationthe filtrate was concentrated in vacuo
8. customThe residue was purified by column chromatography (SiO2, heptane/EtOAc)
9. customto yield a colourless oil, (6.38 g, 60%)

ORD record

ord-e2466af170fa44f9b1755821bbea11b8

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08604061B2