Sodium Carbonate → Methyl 3-bromo-5-(4-fluorophenyl)benzoate

Temperatur

88 °C

To a solution of methyl 3,5-dibromobenzoate (3.00 g, 10.2 mmol) and 4-fluoro-phenyl boronic acid (1.43 g, 10.2 mmol) in 2-methoxyethyl ether (60 ml) and ethanol (3 ml) was added Na2CO3 (saturated, 9 ml), followed by tetrakis(triphenylphosphine) palladium (0) (0.2 g). The mixture was heated at 88° C. for 1.5 h, then cooled to room temperature, partitioned between hexane and water, and the organic phase washed with brine, dried over anhydrous sodium sulfate, decanted, and the organic solution concentrated under reduced pressure. The residue was purified by silica gel chromatography (1% EtOAc in hexane) to yield methyl 3-bromo-5-(4-fluorophenyl)benzoate (intermediate XXXIVa, 0.725 g, 23%) as a white solid, and methyl 3,5-di(4-fluorophenyl)benzoate (intermediate XXXIVb, 0.128 g, 4%) as a white solid.

1. temperaturecooled to room temperature
2. custompartitioned between hexane and water
3. washthe organic phase washed with brine
4. dry with materialdried over anhydrous sodium sulfate
5. customdecanted
6. concentrationthe organic solution concentrated under reduced pressure
7. customThe residue was purified by silica gel chromatography (1% EtOAc in hexane)

ORD-Eintrag

ord-f7d2824e37d748efbaa5e49b5eac6485

Quelldatensatz

uspto-grants-2009_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07491821B2