4-Chloro-2-nitrophenol → HCID 58056182, compound

Temperature

80 °C

Sodium hydride (60% suspension in mineral oil, 0.15 g, 3.75 mmol) was added, at room temperature, to a solution of 4-chloro-2-nitrophenol (0.5 g, 2.88 mmol) in anhydrous N,N-dimethylformamide (15 mL) and the resulting mixture was stirred for 5 minutes. 1-Bromo-3-methoxy-propane (0.485 g, 3.17 mmol) was then added and the reaction mixture was heated at 80° C. for 62 hours. The resulting mixture was partitioned between an aqueous solution of sodium hydroxide (3 M) and ethyl acetate, the organic layer was separated, washed twice with an aqueous solution of sodium hydroxide (3 M) and once with brine, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The crude residue was purified by flash chromatography (hexane/EtOAc, 90/10 to 50/50) to give 0.455 g (64% yield) of 4-chloro-1-(3-methoxy-propoxy)-2-nitro-benzene as a yellow solid.

1. customThe resulting mixture was partitioned between an aqueous solution of sodium hydroxide (3 M) and ethyl acetate
2. customthe organic layer was separated
3. washwashed twice with an aqueous solution of sodium hydroxide (3 M) and once with brine
4. dry with materialdried over anhydrous sodium sulfate
5. filtrationfiltered
6. customevaporated under reduced pressure
7. customThe crude residue was purified by flash chromatography (hexane/EtOAc, 90/10 to 50/50)

ORD record

ord-758e5c16a3cc4160b0756bb9b14fd0be

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09255110B2