Hydrochloric Acid → 4-(Bromomethyl)-1-naphthaldehyde

Temperatur

0 °C

To a stirred solution of 4-(bromomethyl)-1-naphthonitrile (8 g, 33 mmol) in toluene (100 mL) at 0° C. was added dropwise DIBAL-H (1.0 M solution in toluene; 43 mL), and the reaction mixture was stirred at 0° C. for 1 h. 3 N HCl in water (50 mL) was added to the mixture until it became a white slurry and then additional 1 N HCl (20 mL) was added. The organic layer was collected and the aqueous layer was extracted with EtOAc (3 x100 mL). The combined organic layer was dried over Na2SO4 and concentrated under reduced pressure. Purification by flash column chromatography (SiO2, 100-200 mesh; 5% EtOAc in petroleum ether) afforded the title compound as a white solid (7 g, 88%): mp 115-116° C.; 1H NMR (400 MHz, CDCl3) δ 10.41 (s, 1H), 9.35 (m, 1H), 8.22 (m, 1H), 7.90 (d, J=8.0 Hz, 1H), 7.75 (m, 3H), 4.95 (s, 2H); ESIMS m/z 248.88 ([M+H]+).

1. customThe organic layer was collected
2. extractionthe aqueous layer was extracted with EtOAc (3 x100 mL)
3. dry with materialThe combined organic layer was dried over Na2SO4
4. concentrationconcentrated under reduced pressure
5. customPurification by flash column chromatography (SiO2, 100-200 mesh; 5% EtOAc in petroleum ether)

ORD-Eintrag

ord-60e705ad11b742a7a0f815eb374f1ad6

Quelldatensatz

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09226500B2