Boron tribromide → 4-((5-Bromo-2-chlorophenyl)methyl)phenol

Temperature

0 °C

4-bromo-1-chloro-2-(4-methoxybenzyl)-benzene (10 g, 32 mmol) was dissolved in dichloromethane (32 mL) and cooled to 0° C. under nitrogen. A 1.0 M boron tribromide solution in dichloromethane (35.3 mL, 34.3 mmol) was added dropwise over 10 minutes. Following the addition, the ice bath was removed and the solution was stirred at room temperature for 1 hour. The reaction mixture was cooled to 0° C. and quenched by addition of 1N aqueous hydrochloric acid solution (45 mL). The mixture was stirred for 30 minutes, transferred to a separatory funnel, the organic layer was collected, and the aqueous layer was extracted with dichloromethane (45 mL). The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 4-(5-bromo-2-chlorobenzyl)phenol (9.5 g, 99% yield) as a white solid.

1. additionthe addition
2. customthe ice bath was removed
3. temperatureThe reaction mixture was cooled to 0° C.
4. customquenched by addition of 1N aqueous hydrochloric acid solution (45 mL)
5. stirringThe mixture was stirred for 30 minutes
6. customtransferred to a separatory funnel
7. customthe organic layer was collected
8. extractionthe aqueous layer was extracted with dichloromethane (45 mL)
9. dry with materialThe combined organic extracts were dried over magnesium sulfate
10. filtrationfiltered
11. concentrationconcentrated in vacuo

ORD record

ord-25d4e208dda246259b97ad09aee42eca

Source dataset

uspto-grants-2011_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08080580B2