1-Chloro-3-iodopropane → HCID 19786581, compound

Temperature

-78 °C

In a similar manner to that of Examples 7a-d starting with 4-chlorobenzaldehyde oxime, the starting ketone is prepared. In 220 ml anhydrous THF was dissolved 8.1 g 3-(4-chlorophenyl)-6,7-dihydro-1,2-benzisoxazol-4(5H)-one under nitrogen atmosphere with stirring. The solution was cooled to -78° C. and 32.8 ml lithium diisopropylamide (1.5 molar in cyclohexane) was added dropwise. The resulting solution was stirred for fifteen minutes at -78° C. and 4.6 ml 1-chloro-3-iodopropane was added. Upon warming to room temperature, the reaction mixture was poured into water and the layers were separated. The aqueous phase was extracted twice with dichloromethane and once with ether. The combined organic layers were washed with brine and dried (MgSO4). Filtration and concentration gave the crude product. Column chromatography on silica gel (start with 5% dichloromethane in hexane and gradually increase polarity to 100% dichloromethane) gave 5.2 g of 3-(4-chlorophenyl)-5-(3-chloropropyl)-6,7-dihydro-1,2-benzisoxazol-4 (5H)-one.

1. stirringThe resulting solution was stirred for fifteen minutes at -78° C.
2. temperatureUpon warming to room temperature
3. customthe layers were separated
4. extractionThe aqueous phase was extracted twice with dichloromethane and once with ether
5. washThe combined organic layers were washed with brine
6. dry with materialdried (MgSO4)
7. filtrationFiltration and concentration
8. customgave the crude product

ORD record

ord-be8378ed7df54e1d838578c3661c2c9d

Source dataset

uspto-grants-1992_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05114936