Tetrahydrofuran → 2-Bromo-1-[3-methoxy-5-(pentafluorosulfanyl)phenyl]ethanone

1-[3-Methoxy-5-(pentafluorosulfanyl)phenyl]ethanone (34 mg) was dissolved in absolute methanol (3 ml). To this were added, while stirring, DL-camphorsulfonic acid (0.6 mg) and trimethyl orthoformate (40 mg). After stirring for 4 h, the mixture was left to stand overnight and then absolute THF (3 ml) and phenyltrimethylammonium tribromide (40 mg) were added while stirring. After stirring at RT for 2 h, the mixture was stirred at 50° C. for 3 h, left to stand over the weekend and, after adding further phenyltrimethylammonium tribromide (20 mg), stirred at 50° C. for another 5 h. The reaction mixture was concentrated, and the residue was taken up with acetonitrile and admixed with 5N sulfuric acid while stirring. After stirring for 2 h, the mixture was concentrated and the residue was purified by means of preparative HPLC. The product-containing fractions were combined, freed of the acetonitrile, admixed with saturated sodium hydrogencarbonate solution and extracted three times with ethyl acetate. The combined extracts were dried over magnesium sulfate, filtered and concentrated. 15 mg of the desired compound were obtained.

1. additionTo this were added
2. stirringAfter stirring for 4 h
3. waitthe mixture was left
4. stirringwhile stirring
5. stirringAfter stirring at RT for 2 h
6. stirringthe mixture was stirred at 50° C. for 3 h
7. waitleft
8. stirringstirred at 50° C. for another 5 h
9. concentrationThe reaction mixture was concentrated
10. stirringwhile stirring
11. stirringAfter stirring for 2 h
12. concentrationthe mixture was concentrated
13. customthe residue was purified by means of preparative HPLC
14. extractionextracted three times with ethyl acetate
15. dry with materialThe combined extracts were dried over magnesium sulfate
16. filtrationfiltered
17. concentrationconcentrated

ORDレコード

ord-7c372777d92a437a808988d488722592

出典データセット

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08466169B2