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

温度

-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レコード

ord-ed0abce153fe40dda6727a38841c1c00

出典データセット

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07569601B2