Benzyl Bromide → 5-(Benzyloxy)-2-nitrobenzaldehyde

To a suspension of 5-hydroxy-2-nitrobenzaldehyde (300 mg, 1.80 mmol), potassium carbonate (498 mg, 3.60 mmol), and tetrabutylammonium iodide (66 mg, 0.18 mmol) in 1.8 mL of dry N,N-dimethylformamide was added benzyl bromide (0.32 mL, 2.7 mmol) at 0° C. After being stirred at room temperature until the starting material disappeared (5 h), the reaction mixture was filtered to remove inorganic salts. The filtrate was diluted with diethyl ether, and the solution was washed with water, saturated NaHCO3 aqueous solution, brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10 to 75/25) to obtain the title compound as a slightly yellow solid (405 mg, 87%).

1. custom(5 h)
2. filtrationthe reaction mixture was filtered
3. customto remove inorganic salts
4. additionThe filtrate was diluted with diethyl ether
5. washthe solution was washed with water, saturated NaHCO3 aqueous solution, brine
6. dry with materialdried over MgSO4
7. filtrationAfter filtration
8. concentrationthe filtrate was concentrated in vacuo
9. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=90/10 to 75/25)

ORD record

ord-ecea00dc8af24c10a89f28789974b9a3

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08552220B2