2-Bromo-5-fluorobenzaldehyde → HCID 58140257, compound

Temperature

0 °C

To a solution of 2-bromo-5-fluoro-benzaldehyde (17.0 g, 83.7 mmol) in tetrahydrofuran (100 mL), cooled to 0° C. under nitrogen, was added methyl magnesium chloride solution (3M in tetrahydrofuran, 31.0 mL, 93.0 mmol, 1.1 eq.) dropwise over a 20 min period. The resulting solution was stirred at 0° C. for 45 min before quenching with aqueous ammonium chloride solution (1M, 17 mL). The resulting mixture was partitioned between pentane (300 mL) and water (100 mL). The organic phase was washed with brine (50 mL) and then dried over magnesium sulphate. This mixture was filtered and concentrated under reduced pressure. The residue was purified by chromatography on silica gel eluting with a gradient of toluene in pentane (50:50 to 100:0 by volume) to produce the title compound as a colourless oil (13.8 g, 75%).

1. custombefore quenching with aqueous ammonium chloride solution (1M, 17 mL)
2. customThe resulting mixture was partitioned between pentane (300 mL) and water (100 mL)
3. washThe organic phase was washed with brine (50 mL)
4. dry with materialdried over magnesium sulphate
5. filtrationThis mixture was filtered
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by chromatography on silica gel eluting with a gradient of toluene in pentane (50:50 to 100:0 by volume)

ORD record

ord-60d25aaef0ac470b8a8a73fa7b27693f

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08916593B2