Reaktion #45466

Reaktionsgleichung

4-chlorofuro[3,2-c]pyridine

bromine

→

title compound

Ausbeute 96.3%

3-Bromo-4-chlorofuro[3,2-c]pyridine

Ausbeute 96.3%

Lösungsmittel

carbon tetrachloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvent was removed in vacuo
2. 2
   workup.DISSOLUTIONthe residue was dissolved in methanol (250 mL)
3. 3
   workup.ADDITIONA solution of 20% aqueous sodium hydroxide (35 mL) was added
4. 4
   workup.STIRRINGthe mixture was stirred 1 hour at ambient temperature
5. 5
   SonstigeThe methanol was removed in vacuo
6. 6
   Sonstigethe residue was partitioned between water (100 mL) and dichloromethane (50 mL)
7. 7
   SonstigeThe layers were separated
8. 8
   Extraktionthe aqueous phase was extracted with dichloromethane (50 mL)
9. 9
   TrocknenThe combined organic layers were dried over anhydrous magnesium sulfate
10. 10
    Sonstigethe solvent was removed in vacuo

Vorschrift

A solution of 4-chlorofuro[3,2-c]pyridine (10.60 g, 69 mmol, 1.0 eq) in carbon tetrachloride (135 mL) was cooled to −15° C. and bromine (12.13 g, 80 mmol, 1.2 eq) was added drop-wise over a fifteen minute time period. The mixture was stirred at ambient temperature for eighteen hours. The solvent was removed in vacuo, and the residue was dissolved in methanol (250 mL). A solution of 20% aqueous sodium hydroxide (35 mL) was added and the mixture was stirred 1 hour at ambient temperature. The methanol was removed in vacuo, and the residue was partitioned between water (100 mL) and dichloromethane (50 mL). The layers were separated and the aqueous phase was extracted with dichloromethane (50 mL). The combined organic layers were dried over anhydrous magnesium sulfate and the solvent was removed in vacuo to give the title compound (15.45 g, 96%) as a solid. 1H NMR (DMSO-d6,400 MHz) δ 8.54 (s, 1H), 8.37 (d, 1H), 7.87 (d, 1H); RP-HPLC (Conditions f) Rt 11.46 min.; MS: MH+ 232, 234.

Quelle