Acetaminophen → HCID 23274180, compound

TEA (0.28 ml, 1.98 mmol, 3.0 eq) was added to a solution of paracetamol [4147] (0.10 g, 0.66 mmol, 1.0 eq) of in dry THF under argon atmosphere. At 0° C., bromoacetyl chloride [244] (0.123 g, 0.79 mmol, 1.2 eq) was added. The reaction mixture was stirred at room temperature for 24 h. After 24 h, solvent was evaporated under vacuum and residue was taken in dichloromethane (50 ml) and washed with a 10% solution of NaHCO3 (15 ml) and then with brine (10 ml), followed by drying of the organic layer over anhydrous sodium sulfate. Evaporation of the solvent provided white solid which was purified by silica gel column chromatography (0.5% MeOH: DCM, 100-200 mesh silica) to give the product 4-acetamidophenyl 2-bromoacetate [299] (0.05 g, 28%).

1. waitAfter 24 h
2. customsolvent was evaporated under vacuum and residue
3. washwashed with a 10% solution of NaHCO3 (15 ml)
4. dry with materialby drying of the organic layer over anhydrous sodium sulfate
5. customEvaporation of the solvent
6. customprovided white solid which
7. customwas purified by silica gel column chromatography (0.5% MeOH: DCM, 100-200 mesh silica)

ORD record

ord-e224ca4ec0304ef0bf0a4dc715b5ec3b

Source dataset

uspto-grants-2016_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09359376B2