Hydrochloric Acid → HCID 57321314, compound

Butyl lithium (2.4M, 11 ml) in hexane was added over a period of 5 minutes to a solution of diethyl 4-bromophenyl-ethoxymethylphosphonate (10.11 g, 30 mmol) in tetrahydrofuran (150 ml) at 78° C. under an atmosphere of nitrogen. After 10 minutes stirring, a solution of N-methyl 5-imidazolecarboxaldehyde (2.2 g) in tetrahydrofuran (80 ml) was added and the reaction mixture was allowed to warm slowly to room temperature. Water (200 ml) and concentrated hydrochloric acid (25 ml) were added and the reaction mixture was refluxed for 4 hours and then cooled to room temperature. The reaction mixture was then neutralised with anhydrous sodium carbonate and the tetrahydrofuran evaporated. The residue was extracted with ethyl acetate (3×300 ml) and the combined organic extract was then washed with saturated sodium chloride solution, dried and concentrated by evaporating off the solvent. Flash chromatography of the residue on silica gel using 9:1 chloroform:methanol as eluant gave 4-bromophenyl 1-methyl-5-imidazolylmethyl ketone (4.9 g) as a white solid, m.pt. 109° C.

1. temperaturethe reaction mixture was refluxed for 4 hours
2. temperaturecooled to room temperature
3. customthe tetrahydrofuran evaporated
4. extractionThe residue was extracted with ethyl acetate (3×300 ml)
5. extractionthe combined organic extract
6. washwas then washed with saturated sodium chloride solution
7. customdried
8. concentrationconcentrated
9. customby evaporating off the solvent

ORD record

ord-488ec1604eba44baad3e5b479c7029bf

Source dataset

uspto-grants-1990_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04914120