HCID 64013110, Verbindung → 4-Bromo-7-chloro-1-benzofuran

Temperatur

90 °C

To 80 mL of benzene was added polyphosphoric acid (3.47 g, 36.9 mmol) and commercially available 2-(5-bromo-2-chlorophenoxy)acetaldehyde (9.2 g, 36.9 mmol) and separated into eight 20 mL vials containing equal amounts. The vials were heated with an external temperature of 90° C. for 4 days. Upon cooling of the reaction, the benzene was removed by decanting. Celite (50 g) was added to the organic solution and the solvent was removed using a rotary evaporator. The impregnated Celite was loaded onto a Teledyne-Isco purification system and purified by silica gel chromatography using 0-30% ethyl acetate:hexanes to give 4-bromo-7-chlorobenzofuran as a white solid (2.7 g, 32%): 1H NMR (400 MHz, CDCl3) δ 7.73 (d, J=2.2 Hz, 1H), 7.33 (d, J=8.3 Hz, 1H), 7.18 (d, J=8.3 Hz, 1H), 6.85 (d, J=2.2 Hz, 1H); 13C NMR (101 MHz, CDCl3) δ 150.38 (s), 146.14 (s), 130.27 (s), 126.56 (s), 125.32 (s), 116.44 (s), 112.49 (s), 107.71 (s); ESIMS m/z 232 ([M+H]+), 230 ([M−H]−).

1. customseparated into eight 20 mL vials
2. additioncontaining equal amounts
3. temperatureUpon cooling of the reaction
4. customthe benzene was removed
5. customby decanting
6. additionCelite (50 g) was added to the organic solution
7. customthe solvent was removed
8. customa rotary evaporator
9. customThe impregnated Celite was loaded onto a Teledyne-Isco purification system
10. custompurified by silica gel chromatography

ORD-Eintrag

ord-38b41b9d0ba64e64b7ee31a425e3b091

Quelldatensatz

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09278985B2