Bromine → HCID 21189372, compound

Into a 500 mL round bottom flask containing a 2.5 cm stirring bar was added 13 g of 7-(γ-bromopropyloxy)coumarin and 120-150 mL of THF. When the 7-(γ-bromopropyloxy)coumarin was completely dissolved, 3 mL of bromine was added by syringe. After stirring for 2-5 hours at room temperature, the solution was concentrated by rotary evaporator. 50 mL of a 1:1 mixture of ethyl acetate and hexane was added to the concentrate and the mixture was stirred for 30 minutes at room temperature. The solution was then filtered and the solids washed 3 times with 1:1 ethyl acetate and hexane and then dried for 2 hours. To obtain additional product, the filtrate was concentrated by rotary evaporator and 30 mL of a 1:1 mixture of ethyl acetate and hexane was added to the concentrate. The resulting mixture was then filtered, the solids washed three times with 1:1 ethyl acetate and hexane and then dried for 2-5 hours. The product was checked by TLC (ethyl acetate:hexane (4:6)).

1. additionInto a 500 mL round bottom flask containing a 2.5 cm
2. stirringAfter stirring for 2-5 hours at room temperature
3. concentrationthe solution was concentrated by rotary evaporator
4. addition50 mL of a 1:1 mixture of ethyl acetate and hexane
5. additionwas added to the
6. concentrationconcentrate
7. stirringthe mixture was stirred for 30 minutes at room temperature
8. filtrationThe solution was then filtered
9. washthe solids washed 3 times with 1:1 ethyl acetate and hexane
10. customdried for 2 hours
11. customTo obtain additional product
12. concentrationthe filtrate was concentrated by rotary evaporator and 30 mL of a 1:1 mixture of ethyl acetate and hexane
13. additionwas added to the concentrate
14. filtrationThe resulting mixture was then filtered
15. washthe solids washed three times with 1:1 ethyl acetate and hexane
16. customdried for 2-5 hours

ORD record

ord-c927cde83e6449e08d74ebd74a83dfd9

Source dataset

uspto-grants-1999_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05869701