Imidazole → 4'-Chloro-2-(iodomethyl)biphenyl

Triphenylphosphine (8.47 g, 32.3 mmol), iodine (8.94 g, 35.2 mmol), imidazole (2.40 g, 352 mmol), and CH2Cl2 (110 mL) were combined in a round-bottom flask, and the mixture was stirred for 15 minutes. A solution of (4′-chloro-biphenyl-2-yl)-methanol in CH2Cl2 (40 mL) was then added, and the reaction was stirred at room temperature for 16 hours (flask was wrapped in aluminum foil to shield it from the light). A saturated aqueous Na2S2O2 was added. The layers were separated, and the aqueous layer was extracted with CH2Cl2 (2×100 mL). The organic layers were combined, dried over MgSO4, and concentrated. The crude residue was purified by flash chromatography on silica gel (0-10% EtOAc/heptanes) to afford the title compound as an off-white solid (5.33 g, 55% yield). 1H NMR (400 MHz, CDCl3) δ ppm 7.51-7.53 (m, 1H), 7.38-7.46 (m, 4H), 7.28-7.37 (m, 2H); 7.15-7.17 (m, 1H).

1. stirringthe reaction was stirred at room temperature for 16 hours (flask
2. customThe layers were separated
3. extractionthe aqueous layer was extracted with CH2Cl2 (2×100 mL)
4. dry with materialdried over MgSO4
5. concentrationconcentrated
6. customThe crude residue was purified by flash chromatography on silica gel (0-10% EtOAc/heptanes)

ORD record

ord-d6d20621b1624f64bfa8fe3b53015dba

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08809352B2