1-(2-Bromophenyl)ethan-1-ol → (1S)-1-(2-iodophenyl)ethanol

Temperature

150 °C

To each of three identical Emrys microwave reaction vessels was added (S)-1-(2-bromophenyl)ethanol (1.67 g, 8.3 mmol), CuI (189 mg, 1.0 mmol), 1,4-dioxane (12.4 ml), N,N′-dimethylethylenediamine (0.18 ml, 1.7 mmol) and sodium iodide dihydrate (3.1 g, 16.6 mmol). Each vessel was sealed and heated in an Emrys microwave reactor to 150° C. for 2 h. On cooling, the mixtures were combined and partitioned between water (20 ml) and EtOAc (20 ml). The organic phase was washed with brine (20 ml), dried (MgSO4), filtered, and concentrated in vacuo. The crude product was taken up in isohexane (50 ml) and the solution held at −15° C. for 16 h to afford (S)-1-(2-iodophenyl)ethanol as a white crystalline solid (4.95 g).

1. customTo each of three identical Emrys microwave reaction vessels
2. customEach vessel was sealed
3. temperatureOn cooling
4. custompartitioned between water (20 ml) and EtOAc (20 ml)
5. washThe organic phase was washed with brine (20 ml)
6. dry with materialdried (MgSO4)
7. filtrationfiltered
8. concentrationconcentrated in vacuo

ORD record

ord-69de509636014e999f9b79851edd5e22

Source dataset

uspto-grants-2008_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07468393B2