Réaction #48343

Équation de réaction

(3-Bromo-4-fluorophenyl)methanol

tribromoborane

→

title compound

2-Bromo-4-(bromomethyl)-1-fluorobenzene

Solvants

DCM

Conditions de réaction

Traitement

1. 1
   TempératureThe solution was cooled to 0 deg
2. 2
   workup.WAITrt for 1 h
3. 3
   AutreThe reaction was quenched with water
4. 4
   Autrethe mixture was transferred to a separatory funnel with half-saturated NaHCO3 (15 mL)
5. 5
   Extractionthe aqueous phase was extracted with DCM (3×20 mL)
6. 6
   Lavagewashed with half-saturated brine (5 mL)
7. 7
   Séchagedried over sodium sulfate
8. 8
   Concentrationconcentrated
9. 9
   AutrePurification of the residue through silica gel (40 mL)

Mode opératoire

(3-Bromo-4-fluorophenyl)methanol (0.264 g, 1.29 mmol) was dissolved in DCM (3 mL). The solution was cooled to 0 deg, and tribromoborane (1.0 M in DCM, 0.863 ml, 0.863 mmol) was added. The mixture was stirred at 0 deg for 1 h, then rt for 1 h. The reaction was quenched with water, and the mixture was transferred to a separatory funnel with half-saturated NaHCO3 (15 mL), and the aqueous phase was extracted with DCM (3×20 mL). The organics were combined, washed with half-saturated brine (5 mL), dried over sodium sulfate and concentrated. Purification of the residue through silica gel (40 mL) using 5% EtOAc-hexane afforded the title compound.

Source