Boron tribromide → Methyl 3-(3-hydroxyphenyl)benzoate

Temperature

-78 °C

To a −78° C. solution of methyl 3-(3-methoxyphenyl)-benzoate (1.48 g) in anhydrous methylene chloride (16 mL) was added dropwise a solution of boron tribromide in methylene chloride (1.0 M, 16.3 mL). The mixture was stirred at −78° C. for 30 min, allowed to warm to 0° C., and stirred for 2 h. The mixture was quenched by addition of saturated aqueous sodium bicarbonate (50 mL), and diluted with methylene chloride (50 mL). The mixture was placed in a separatory funnel, and the organic layer was separated, dried over sodium sulfate, filtered and concentrated to give the crude product. Purification by silica gel chromatography (eluting with 5:1 hexanes/ethyl acetate) afforded the title compound (769 mg) as a pale yellow oil.

1. temperatureto warm to 0° C.
2. stirringstirred for 2 h
3. customThe mixture was quenched by addition of saturated aqueous sodium bicarbonate (50 mL)
4. additiondiluted with methylene chloride (50 mL)
5. customThe mixture was placed in a separatory funnel
6. customthe organic layer was separated
7. dry with materialdried over sodium sulfate
8. filtrationfiltered
9. concentrationconcentrated
10. customto give the crude product
11. customPurification
12. washby silica gel chromatography (eluting with 5:1 hexanes/ethyl acetate)

ORD record

ord-a830c2bd6c4b40c98a5ea2878bb4ab03

Source dataset

uspto-grants-2001_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06251925B1