Triisopropyl borate → HCID 86685467, compound

Temperature

-78 °C

To a solution of 2-bromo-1-(3-(methoxymethoxy)pentan-3-yl)-4-methylbenzene (3.0 g, 10 mmol) in THF (80 mL) cooled at −78° C. was added n-BuLi (12 mL, 30 mmol) dropwise. The mixture was stirred at −78° C. for additional 1 h and then triisopropyl borate (3.76 g, 20 mmol) in 5 mL of THF was added below −70° C. The resulting mixture was kept stirring at −78° C. for 30 min and allowed to warm to rt and stirred overnight. Then it was quenched with aqueous NH4Cl and extracted with ethyl acetate. The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography to provide the product (0.8 g, 39.2%). 1H NMR (400 MHz, DMSO-d6): δ 8.92 (s, 1 H), 7.43 (s, 1 H), 7.23 (s, 1 H), 7.12 (s, 1 H), 2.3 (s, 3 H), 1.83-1.63 (m, 4 H), 0.50 (t, 6 H) ppm.

1. stirringThe resulting mixture was kept stirring at −78° C. for 30 min
2. temperatureto warm to rt
3. stirringstirred overnight
4. customThen it was quenched with aqueous NH4Cl
5. extractionextracted with ethyl acetate
6. dry with materialThe organic layer was dried over Na2SO4
7. concentrationconcentrated under reduced pressure
8. customThe residue was purified by column chromatography

ORD record

ord-d9e75da6fb794f29b2fc42c16831f6dd

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08546357B2