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 trifluoromethanesulfonic 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-5aac9cbb89d841b6b4bf2680db400ac6

Source dataset

uspto-grants-2009_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07582645B2