Acetic Anhydride → 1-(2-Methoxy-5-trifluoromethylphenyl)ethanone

2′-methoxy-5′-trifluoromethyl-acetophenone was prepared as follow (US2003/0109574): In a water bath at room temperature, to a solution of trifluoromethane sulfonic acid (5 ml, 56.7 mmol) under argon was slowly added a solution of 4-trifluoromethyl-anisol (2.0 g, 11.35 mmol) in acetic anhydride (2.15 ml, 22.7 mmol). The resulting dark mixture was stirred for 3 hours at room temperature then poured onto ice water (26 ml). The product was extracted several times with ether. The ethereal layer was washed with a 10% solution of sodium hydrogenocarbonate, water, dried over sodium sulfate and concentrated to dryness. The residue was purified by flash chromatography over silica gel (gradient cyclohexane/dichloromethane: 0-50%) to yield 2′-methoxy-5′-trifluoromethyl-acetophenone (1.7 g, 67%) as a white solid.

1. custom2′-methoxy-5′-trifluoromethyl-acetophenone was prepared
2. additionthen poured onto ice water (26 ml)
3. extractionThe product was extracted several times with ether
4. washThe ethereal layer was washed with a 10% solution of sodium hydrogenocarbonate, water
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated to dryness
7. customThe residue was purified by flash chromatography over silica gel (gradient cyclohexane/dichloromethane: 0-50%)

ORD record

ord-e7f453f1fdff4b53b5c4e6398e931749

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08962627B2