Water → 2-(3-nitrophenoxy)ethanol

Temperature

70 °C

A solution of m-nitrophenol (2.0 g, 14 mmol), 2-bromoethanol (1.4 mL, 20 mmol), and potassium carbonate (3.0 g, 22 mmol) in N,N-dimethylformamide (10 mL) was heated at 70° C. for 7 h. The reaction mixture was treated with additional 2-bromoethanol (0.5 mL, 7.2 mmol) and potassium carbonate (1.0 g, 7.2 mmol) and heated at 70° C. for 20 h. The reaction mixture was poured into water (50 mL) and extracted with ethyl acetate (150 mL). The organic layer was separated and washed with brine (50 mL), dried over anhydrous sodium sulfate, filtered, and evaporated to a crude residue. This material was purified by flash column chromatography to give the desired product (1.9 g, 70%) as a white solid. LCMS for C8H10NO4 (M+H)+: m/z=183.9.

1. extractionextracted with ethyl acetate (150 mL)
2. customThe organic layer was separated
3. washwashed with brine (50 mL)
4. dry with materialdried over anhydrous sodium sulfate
5. filtrationfiltered
6. customevaporated to a crude residue
7. customThis material was purified by flash column chromatography

ORD record

ord-b6d43b2d19f94bbdb4c24b9ac8a95d34

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08871753B2