Iodine → 4-Bromo-2-ethoxy-1-iodobenzene

To a solution of 62B (2.5 g, 1.2 mmol) in acetonitrile (30 mL) at 0° C. was added dropwise a solution of iodine (6 g, 2.4 mmol), and t-BuONO (1.44 g, 1.4 mmol) in acetonitrile (100 mL) over 30 min and stirred 1.5 h. The mixture was quenched with aqueous Na2SO3 while maintaining the temperature <10° C. After stirring 1 h the mixture was extracted with hexane (3×100 mL). The combined organics were dried (MgSO4) before concentrating in vacuo and the residue was purified by flash chromatography (0-5% EtOAc/Hexane) to afford 62C (2 g, 53%) as an oil. 1H NMR (400 MHz, CDCl3) δ ppm 1.47 (t, J=7.03 Hz, 4 H) 4.06 (q, J=7.03 Hz, 2 H) 6.83 (dd, J=8.35, 1.76 Hz, 1 H) 6.90 (d, J=2.20 Hz, 1 H) 7.59 (d, J=8.35 Hz, 1 H).

1. customThe mixture was quenched with aqueous Na2SO3
2. temperaturewhile maintaining the temperature <10° C
3. stirringAfter stirring 1 h the mixture
4. extractionwas extracted with hexane (3×100 mL)
5. dry with materialThe combined organics were dried (MgSO4)
6. concentrationbefore concentrating in vacuo
7. customthe residue was purified by flash chromatography (0-5% EtOAc/Hexane)

ORD record

ord-e3eed22c3ac1407290d5117a6b8e7c99

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07592331B2