Triethylsilane → 4-[(4-Fluorophenyl)methyl]aniline

To a solution of (4-fluoro-phenyl)-(4-nitrophenyl)-methanone (2.0 g, 8.2 mmol) in dichloromethane (16 mL) at, 0° C. was added trifluromethanesulfonic acid (1.4 mL, 16 mmol) in dichloromethane (16 mL). A solution of triethylsilane (2 mL, 12 mmol) in dichloromethane (16 mL) was subsequently added dropwise, resulting in an exotherm. After 5 min, additional trifluoromethanesulfonic acid (1.4 mL, 16 mmol) was added, followed by triethylsilane (2.0 mL, 12 mmol). The reaction mixture was stirred at rt for 2 h, then poured into cold saturated sodium bicarbonate and extracted several times with dichloromethane. The combined organic extracts were dried over sodium sulfate and concentrated in vacuo. Purification by column chromatography eluting with 0-10% ethyl acetate in hexanes, gave the desired product as a white solid (260 mg, 14%). 1H NMR (CHCl3-d) δ 8.14 (m, 2H), 7.31 (m, 2H), 7.12 (m, 2H), 7.01 (m, 2H), 4.06 (s, 2H).

1. customresulting in an exotherm
2. extractionextracted several times with dichloromethane
3. dry with materialThe combined organic extracts were dried over sodium sulfate
4. concentrationconcentrated in vacuo
5. customPurification by column chromatography
6. washeluting with 0-10% ethyl acetate in hexanes

ORD record

ord-fe74df113b9f4606ad1e051ec9f25dcd

Source dataset

uspto-grants-2010_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07678804B2