Hydrochloric Acid → 4-Cyano-3-methoxyphenylboronic acid

Temperature

-78 °C

A 3-necked 1 L round-bottomed flask was equipped with an overhead stirrer, and a nitrogen line. The flask was charged with 45.56 g (215 mmol) of 4-bromo-2-methoxybenzonitrile, 64 mL (277 mmol) of tri-isopropylborate and 500 mL of THF. The solution was cooled to −78° C. in a dry-ice/acetone bath. n-Butyllithium (2.5M, 110 mL, 275 mmol) was added dropwise via addition funnel. The mixture was stirred for 30 minutes and 2N HCl was added. The mixture was stirred for an hour and poured into water. The mixture was extracted with Et2O. The organic solution was backextracted with 1N NaOH. The aqueous layer was washed with Et2O and acidified with conc. HCl. The mixture was extracted with Et2O. The organic extract was dried (MgSO4) and evaporated in vacuo to afford 20.77 g (55%) of the product as a white solid. 1H NMR (500 MHz, d6-DMSO) δ 7.68 (d, 1H), 7.59 (s, 1H), 7.47 (d, 1H), 3.95 (s, 3H).

1. customA 3-necked 1 L round-bottomed flask was equipped with an overhead stirrer
2. stirringThe mixture was stirred for an hour
3. extractionThe mixture was extracted with Et2O
4. washThe aqueous layer was washed with Et2O
5. extractionThe mixture was extracted with Et2O
6. extractionThe organic extract
7. dry with materialwas dried (MgSO4)
8. customevaporated in vacuo

ORD record

ord-03bdf4f2d46542f28ca57e4bd6fb2834

Source dataset

uspto-grants-2014_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08722889B2