Diisobutylaluminum hydride → HCID 39232332, compound

Temperature

-78 °C

4′,6-Dichloro-N-methoxy-N-methylbiphenyl-3-carboxamide (1.0 g, 3.2 mmol, 1.0 eq) was dissolved in dry THF and stirred for 10 minutes. The solution was cooled to −78° C. and DIBAL-H (1 M solution, 1.83 g, 12.9 mmol, 4 eq, 13 mL) was slowly added over 15-30 minutes. The reaction mixture was stirred for 1 h at −78° C., quenched with saturated NH4Cl solution at −78° C. and stirred for 30 minutes at ambient temperature. Water and ethyl acetate were added into the reaction mixture. The aqueous layer was separated and extracted twice with ethyl acetate. The organic layer was dried with anhydrous Na2SO4 and concentrated under vacuum to give the desired product (0.7 g, 87%). 1H NMR (400 MHz, CDCl3) δ 7.06-7.09 (d, 2H), 7.24-7.27 (d, 2H), 7.40 (s, 1H), 7.55-7.58 (d, 1H), 7.90-7.95 (m, 1H).

1. stirringThe reaction mixture was stirred for 1 h at −78° C.
2. customquenched with saturated NH4Cl solution at −78° C.
3. stirringstirred for 30 minutes at ambient temperature
4. additionWater and ethyl acetate were added into the reaction mixture
5. customThe aqueous layer was separated
6. extractionextracted twice with ethyl acetate
7. dry with materialThe organic layer was dried with anhydrous Na2SO4
8. concentrationconcentrated under vacuum

ORD record

ord-2f5ba791826e4ac0b37ff84529f555f9

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08501992B2