Dichloromethane → HCID 86690913, compound

247 mg (1.04 mmol) of the compound from Example 67A together with 185 mg (1.04 mmol) of N-bromosuccinimide and 17 mg (0.10 mmol) of 2,2′-azobis-2-methylpropanenitrile in 3 ml of carbon tetrachloride were heated under reflux for 18 h. For work-up, the reaction mixture was cooled to RT, and 10 ml of dichloromethane were added. The mixture was washed with 5 ml of water, and the aqueous phase was re-extracted twice with in each case 5 ml of dichloromethane. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The crude product was briefly dried under high vacuum and reacted further without further purification. This gave 303 mg of product which contained the target compound in a purity of 20% (corresponds to 20% of theory). The main component of the crude product was unreacted starting material (Example 67A).

1. temperatureunder reflux for 18 h
2. washThe mixture was washed with 5 ml of water
3. extractionthe aqueous phase was re-extracted twice with in each case 5 ml of dichloromethane
4. dry with materialThe combined organic phases were dried over magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. dry with materialThe crude product was briefly dried under high vacuum
8. customreacted further without further purification

ORD record

ord-488aa99a88c5418d94067d884b6b7ade

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09187466B2