Hydrochloric Acid → 1-(3-Dimethylamino-5-pentafluorosulfanylphenyl)ethanone

Temperature

0 °C

3-Dimethylamino-N-methoxy-N-methyl-5-pentafluorosulfanylbenzamide (980 mg) was dissolved in abs. THF (50 ml), and methylmagnesium bromide solution (2.1 ml; 3M solution in diethyl ether) was added dropwise while stirring at 0° C. After the addition had ended, the ice bath was removed and the mixture was stirred at RT for 1 h. To complete the reaction, more methylmagnesium bromide solution (0.3 ml) was added and the mixture was stirred for a further 2 h. After storing overnight in a refrigerator, the reaction mixture was admixed with 1 N hydrochloric acid while cooling. Addition of water and ethyl acetate was followed by extraction twice more with ethyl acetate, and the combined organic phases were dried with magnesium sulfate, filtered and concentrated. The residue was purified by means of chromatography on silica gel (100/0 to 50/50 n-heptane/ethyl acetate within 30 min). The product-containing fractions were combined, the solvent was removed and the residue was dried under high vacuum. 650 mg of the title compound were obtained.

1. additionAfter the addition
2. customthe ice bath was removed
3. stirringthe mixture was stirred at RT for 1 h
4. customthe reaction, more methylmagnesium bromide solution (0.3 ml)
5. additionwas added
6. stirringthe mixture was stirred for a further 2 h
7. temperaturewhile cooling
8. extractionwas followed by extraction twice more with ethyl acetate
9. dry with materialthe combined organic phases were dried with magnesium sulfate
10. filtrationfiltered
11. concentrationconcentrated
12. customThe residue was purified by means of chromatography on silica gel (100/0 to 50/50 n-heptane/ethyl acetate within 30 min)
13. customthe solvent was removed
14. customthe residue was dried under high vacuum

ORD record

ord-2a909b252a254c299873457b2954975f

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08466169B2