Triisopropyl borate → (7-Chloro-1-benzothiophen-2-yl)boronic acid

Temperature

-30 °C

To a solution of 7-chlorobenzo[b]thiophene (1.0 g, 5.92 mmol) in THF (25 mL) at −78° C. was added nbutyllithium (7.41 mL, 11.8 mmol, 1.6 M solution). The reaction was allowed to warm to −30° C. then was cooled back to −78° C. and triisopropyl borate (2.23 g, 11.8 mmol) was added. The mixture was allowed to warm to 0° C., saturated ammonium chloride added and the organic phase separated off and concentrated in vacuo. To the residue was added aqueous sodium hydroxide (10 mL, 2N solution) followed by water (30 mL) and the mixture was washed with DCM. The aqueous phase was acidified with 2N sulfuric acid, and the resulting precipitate isolated by filtration and dried under vacuum to yield 7-chlorobenzo[b]thiophene-2-boronic acid (1.21 g, 96%) as white solid. 1H NMR (400 MHz, CDCl3) δ=7.41 (t, J=7.70 Hz, 1H), 7.50 (d, J=7.70 Hz, 1H), 7.91 (d, J=7.70 Hz, 1H), 8.03 (s, 1H), 8.63 (s, 2H); MS (ES+): m/z 211.86 [M+].

1. temperaturethen was cooled back to −78° C.
2. temperatureto warm to 0° C.
3. customthe organic phase separated off
4. concentrationconcentrated in vacuo
5. additionTo the residue was added aqueous sodium hydroxide (10 mL, 2N solution)
6. washthe mixture was washed with DCM
7. customthe resulting precipitate isolated by filtration
8. customdried under vacuum

ORD record

ord-7608b813ba22472da2c525d4b44edb45

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08796455B2