Sodium Carbonate → (4'-Fluorobiphenyl-2-yl)methanol

Temperatur

115 °C

To a mixture of 4-fluorophenylboronic acid (2.5 g, 13.4 mmol), 2-bromobenzyl alcohol (2.81 g, 20.1 mmol) and Pd(PPh3)4 (0.25 g, 0.216 mmol) in DME (20 mL) is added an aqueous solution of Na2CO3 (11.5 mL, 2.7 M, 31 mmol). The mixture is heated to 115° C. in sealed vessel overnight. The reaction is allowed to cool to room temperature and is diluted with EtOAc and water. The aqueous layer is extracted further with EtOAc (2×). The combined organic layers are washed with water, saturated NH4Cl, brine and dried over Na2SO4. After concentration, the resulting residue is purified by flash chromatography (hexane/CH2Cl2) to give (4′-fluorobiphenyl-2-yl)-methanol as oil. (cas #773871-75-3) 1H NMR (400 MHz, CDCl3) δ (ppm) 7.46-7.43 (m, 1H), 7.32-7.22 (m, 4H), 7.18-7.16 (m, 1H), 7.04-6.99 (m, 2H), 4.48 (d, J=5.5 Hz, 2H), 1.68 (br s, 1H).

1. temperatureto cool to room temperature
2. extractionThe aqueous layer is extracted further with EtOAc (2×)
3. washThe combined organic layers are washed with water, saturated NH4Cl, brine
4. dry with materialdried over Na2SO4
5. concentrationAfter concentration
6. customthe resulting residue is purified by flash chromatography (hexane/CH2Cl2)

ORD-Eintrag

ord-35d1dfceb3c64f939831b842566e1a97

Quelldatensatz

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08835646B2