Water → 2-[(4-Fluorophenyl)methyl]thiophene

Temperatur

0 °C

To a suspension of NaI (8 g, 53 mmol) in CH3CN (100 mL) was added TMSCl (6.8 mL, 54 mmol). The resulting mixture was cooled to 0° C. and treated with (4-fluorophenyl)-2-thienylmethan-1-ol, allowed to warm to room temperature, stirred overnight, then cooled to 0° C. and treated with water. The resulting mixture was extracted with EtOAc. The organic layer was washed with a saturated Na2S2O3 solution, water and a saturated NaCl solution, then concentrated under reduced pressure. The crude product was purified by flash chromatography (hex) to give 2-(4-fluorobenzyl)thiophene (1.89 g, 40% overall yield) as a pink oil: TLC (hex) Rf 0.69; 1H NMR (CDCl3) δ 4.14 (s, 2H), 6.80-6.82 (m, 1H), 6.93-7.04 (s, 3H), 7.16-7.28 (m, 3H).

1. temperatureto warm to room temperature
2. temperaturecooled to 0° C.
3. extractionThe resulting mixture was extracted with EtOAc
4. washThe organic layer was washed with a saturated Na2S2O3 solution, water
5. concentrationa saturated NaCl solution, then concentrated under reduced pressure
6. customThe crude product was purified by flash chromatography (hex)

ORD-Eintrag

ord-3e96d091c70c4eb490447d4661d2aaec

Quelldatensatz

uspto-grants-2004_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06784167B2