Dichloromethane → 4-Bromo-2-(bromomethyl)-1-iodobenzene

To a stirred mixture of (5-Bromo-2-iodo-phenyl)-m-ethanol (9.14 g, 29.2 mmol) in CH3Cl (150 mL) under argon was added 1M PBr3 in CH2Cl2 (35.0 mL, 35.0 mmol). The reaction mixture was stirred at room temperature for 20 min and then poured into a mixture of ice and saturated NaHCO3 solution (300 mL). The pH was adjusted to basic by addition of solid NaHCO3. This aqueous layer was extracted with EtOAc (1×600 mL, 2×400 mL). The combined EtOAc extracts were washed with brine (1×100 mL). The organic layer was dried (MgSO4), filtered and concentrated in vacuo to give 4-bromo-2-bromomethyl-1-iodo-benzene (5.69 g, 52%). 1H NMR (CDCl3): δ 7.68 (d, 1H, J=8.80 Hz), 7.59 (s, 1H), 7.18 (d, 1H, J=8.80 Hz), 4.51 (s, 2H). HPLC: Rt=3.87 min.

1. extractionThis aqueous layer was extracted with EtOAc (1×600 mL, 2×400 mL)
2. washThe combined EtOAc extracts were washed with brine (1×100 mL)
3. dry with materialThe organic layer was dried (MgSO4)
4. filtrationfiltered
5. concentrationconcentrated in vacuo

ORDレコード

ord-3c69d0280538416183f6572674fcf09f

出典データセット

uspto-grants-2008_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07417040B2