Imidazole → Benzene, (2-iodoethyl)-

Iodine (12.0 g, 47.4 mmol) was added in one portion to a solution of 2-phenylethanol (5.11 g, 36.5 mmol), triphenylphosphine (11.47 g, 43.8 mmol) and imidazole (3.48 g, 51.04 mmol) in dichloromethane (250 mL) at 0° C. The resulting mixture was allowed to warm slowly to rt and stir overnight, then was transferred to a separatory funnel and washed with water (2×250 mL), saturated aqueous Na2S2O3 (2×100 mL), water (100 mL), and brine (100 mL). The organic phase was dried over MgSO4, filtered and concentrated to a colorless oil that contained a large amount of white solid. The mixture was treated with heptane (2×50 mL) and was filtered. The filtrate was concentrated and the resulting material was again treated with heptane (2×50 mL) and filtered. The filtrate was concentrated to provide 2-phenylethyl iodide as a clear colorless oil (1.74 g, 19%) that contained a trace amount of triphenylphosphine oxide.

1. customwas transferred to a separatory funnel
2. washwashed with water (2×250 mL), saturated aqueous Na2S2O3 (2×100 mL), water (100 mL), and brine (100 mL)
3. dry with materialThe organic phase was dried over MgSO4
4. filtrationfiltered
5. concentrationconcentrated to a colorless oil that
6. additionThe mixture was treated with heptane (2×50 mL)
7. filtrationwas filtered
8. concentrationThe filtrate was concentrated
9. additionthe resulting material was again treated with heptane (2×50 mL)
10. filtrationfiltered
11. concentrationThe filtrate was concentrated

ORD record

ord-e660ba4c25c4420583f0130e908fb72e

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08026366B2