Boron tribromide → B-(4-Chloro-2-hydroxyphenyl)boronic acid

Temperature

0 °C

To a solution of (4-chloro-2-methoxyphenyl)boronic acid (1.0 g, 5.36 mmol) in dichloromethane (5 mL) at 0° C. was added boron tribromide (1 M in dichloromethane, 10 mL, 10 mmol). The reaction was stirred at 0° C. for 1 hour, then allowed to warm to room temperature and stirred as such for 18 hours. The reaction was quenched carefully with water. The resulting precipitate was collected by filtration, to give a white solid, 260 mg. The layers were separated and the organic layer was dried over Na2SO4 and concentrated in vacuo to give a white solid, 300 mg. The two batches of solid were combined to give the title compound as a white solid, 560 mg, in a 61% yield. This material was taken on to Preparation 18 without purification.

1. temperatureto warm to room temperature
2. stirringstirred as such for 18 hours
3. customThe reaction was quenched carefully with water
4. filtrationThe resulting precipitate was collected by filtration
5. customto give a white solid, 260 mg
6. customThe layers were separated
7. dry with materialthe organic layer was dried over Na2SO4
8. concentrationconcentrated in vacuo
9. customto give a white solid, 300 mg

ORD record

ord-21070a6b447c402ebbd747b9b6617fdd

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08809363B2