2,4-Difluorobenzaldehyde → 4-Fluoro-2-(methylthio)benzaldehyde

Temperature

80 °C

A suspension of 2,4-difluorobenzaldehyde (16 mL, 146 mmol) and sodium thiomethoxide (14 g, 200 mmol) in toluene (200 mL) was stirred at 80° C. for 7 h and 14 h at room temperature. The reaction mixture was diluted with ether (300 mL), washed with water (100 mL), saturated aqueous NaHCO3 (100 mL) and brine (50 mL). The aqueous layers were combined and extracted with ether (2×100 mL). The organic layers were combined and dried over anhydrous Na2SO4, filtered and concentrated to give a viscous oil. This viscous oil was dissolved in ether/hexanes (1:1, v/v) and slowly concentrated on under vacuum. The precipitated white solid was separated by filteration and dried to give 2-methylthio-4-fluorobenzaldehyde (18.7 g, 75% yield). 1HNMR (500 MHz, CDCl3) δ: 10.11 (1H, s), 7.78 (1H, dd, J=8.55, 6.11 Hz), 6.97 (1H, dd, J=10.07, 2.44 Hz), 6.91 (1H, td, J=8.54, 2.44 Hz), 2.45 (3H, s). MS calcd for C8H7FOS (M+H): 171.2. found: 171.6.

1. washwashed with water (100 mL), saturated aqueous NaHCO3 (100 mL) and brine (50 mL)
2. extractionextracted with ether (2×100 mL)
3. dry with materialdried over anhydrous Na2SO4
4. filtrationfiltered
5. concentrationconcentrated
6. customto give a viscous oil
7. concentrationv/v) and slowly concentrated on under vacuum
8. customThe precipitated white solid was separated by filteration
9. customdried

ORD record

ord-468417d2d2ab4859a7e2640bd9e1ad2d

Source dataset

uspto-grants-2006_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07109186B2