Water → 4-Bromo-3'-fluoro-4'-methoxybenzophenone

Temperature

-20 °C

To a stirred solution of 2-fluoro-4-bromoanisole (3.03 g, 14.8 mmol) in anhydrous THF (100 mL) was added n-butyllithium (1.6 M in hexanes, 10.2 mL, 16.3 mol) dropwise at −78° C. The reaction mixture was stirred for 1 h and 80 (4.02 g, 16.3 mmol) dissolved in THF (20 mL) was added dropwise. The reaction mixture was warmed to −20° C. over 1 h, water (100 mL) was added, and the volatiles were removed under reduced pressure. The mixture was extracted with ether (3×100 mL) and the combined extracts were washed with water (100 mL) and brine (100 mL). The mixture was dried over MgSO4 and concentrated. The residue was chromatographed on silica gel (20:1 to 5:1 hexanes:EtOAc) to afford 2.35 g (51%) of 81 as a white crystalline solid. 1H NMR (400 MHz, CDCl3): δ 3.97 (s, 3H), 7.01 (t, J=8.4 Hz, 1H), 7.55-7.62 (m, 6H).

1. additionwas added dropwise
2. customthe volatiles were removed under reduced pressure
3. extractionThe mixture was extracted with ether (3×100 mL)
4. washthe combined extracts were washed with water (100 mL) and brine (100 mL)
5. dry with materialThe mixture was dried over MgSO4
6. concentrationconcentrated
7. customThe residue was chromatographed on silica gel (20:1 to 5:1 hexanes:EtOAc)

ORD record

ord-3b00067bb94c482fb0b9363e14ea9eed

Source dataset

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07560589B2