Hydrochloric Acid → 4-[4-(3-Bromo-benzyloxy)-2-nitro-phenoxy]-phenol

A solution of hydroquinone (276.4 mg, 2.510 mmol) in anhydrous 3.64 mmol) and heated under a nitrogen atmosphere at 120° for 30 minutes. A solution of 4-(3-Bromo-benzyloxy)-1-chloro-2-nitro-benzene (from Example 15A) (774 mg, 2.259 mmol) in dimethylsulfoxide (4 mL) was added dropwise from an addition funnel over a period of 30 minutes at 120°, the mixture was then stirred at this temperature for 1 hour. The reaction was cooled in an ice bath, then poured into ice water (20 mL) and adjusted the pH to 2 with concentrated hydrochloric acid. The mixture was extracted with ethyl ether (3×100 mL), the combined ethereal extracts were washed with water (3×100 mL) and brine (50 mL), dried over anhydrous sodium sulfate, filtered and concentrated by rotary evaporation under vacuum. Purification of the residue by silica gel flash chromatography using 3% ethyl acetate/methylene chloride as eluent afforded the title compound as a dark yellow solid (386 mg, 0.927 mmol, 41%).

1. temperatureThe reaction was cooled in an ice bath
2. extractionThe mixture was extracted with ethyl ether (3×100 mL)
3. washthe combined ethereal extracts were washed with water (3×100 mL) and brine (50 mL)
4. dry with materialdried over anhydrous sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated by rotary evaporation under vacuum
7. customPurification of the residue by silica gel flash chromatography

ORD record

ord-f096e60b268b43e0ad4823998e24a061

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07915411B2