Bromine → 3-Bromo-7-(gamma-bromopropyloxy)coumarin

HRID 439692Notes

Reaction equation

HRID 439692 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:15]=[C:14]2[C:9]([CH:10]=[CH:11][C:12](=[O:16])[O:13]2)=[CH:8][CH:7]=1.[Br:17]Br>C1COCC1>[Br:17][C:11]1[C:12](=[O:16])[O:13][C:14]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[C:6]([O:5][CH2:4][CH2:3][CH2:2][Br:1])[CH:15]=2

Participants

4

Reactant 2

HCID 24408BromineHCID 27571767-(3-bromopropoxy)-2H-chromen-2-one2×

Product 1

HCID 211893723-Bromo-7-(gamma-bromopropyloxy)coumarin

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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)).

Workup

  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

Sources & evidence

ORD record
ord-29cc060fb52b4127a0c7eaa8e8a7a619
Source dataset
uspto-grants-1996_05
Patent number
US05516629

Reaction notes

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