Water → HCID 104366942, compound

Temperature

100 °C

To a solution of 5-bromothiophene-2-carbaldehyde (909 mg, 4.76 mmol) and trifluoroethanol (0.69 mL, 9.52 mmol) in 10 mL dimethylformamide was added potassium carbonate (1.38 g, 10.00 mmol). The resulting suspension was stirred at 100° C. for 20 h before being cooled to room temperature and poured into 50 mL water. Organics were extracted with ether (3×50 mL), washed with water and brine (50 mL each), dried over magnesium sulfate, filtered and concentrated. The crude residue was subjected to chromatography on silica gel with gradient elution (10-20% ethyl acetate in hexanes) to give 5-(2,2,2-trifluoroethoxyl)thiophene-2-carbaldehyde (664 mg, 66%) as an off-white solid. Used without further characterization.

1. temperaturebefore being cooled to room temperature
2. extractionOrganics were extracted with ether (3×50 mL)
3. washwashed with water and brine (50 mL each)
4. dry with materialdried over magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated
7. washThe crude residue was subjected to chromatography on silica gel with gradient elution (10-20% ethyl acetate in hexanes)

ORD record

ord-9d320002f94d4861b5bc60871068598b

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09315495B2