4-Bromoanisole → (4-Methoxyphenyl)boronic acid

To a solution of 4-bromoanisole (2 g) in tetrahydrofuran (THF, 32 ml), which was cooled to -78° C., was added a hexane solution of n-butyllithium (0.83 M, 13.5 ml). The solution was stirred 15 minutes, at which time triisopropyl borate (8.6 ml) was added. The solution was stirred for 15 minutes, at which time the solution was allowed to warm to room temperature. Stirring was continued for 12 hrs. The solution was then washed into a hydrochloric acid solution (1M, 60 ml) with a small amount of THF. This solution was stirred an additional 2 hours, and was then extracted with ethyl acetate. The combined organic layers were washed with brine and dried over sodium sulfate, and the solvent was removed in vacuo to yield a white solid.

1. additionwas added
2. stirringStirring
3. waitwas continued for 12 hrs
4. washThe solution was then washed into a hydrochloric acid solution (1M, 60 ml) with a small amount of THF
5. stirringThis solution was stirred an additional 2 hours
6. extractionwas then extracted with ethyl acetate
7. washThe combined organic layers were washed with brine
8. dry with materialdried over sodium sulfate
9. customthe solvent was removed in vacuo
10. customto yield a white solid

ORD record

ord-70c16a52533044dfae060321e3523306

Source dataset

uspto-grants-1995_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05380460