Bromine → HCID 19972720, compound

HRID 2400163Notes

Reaction equation

HRID 2400163 reaction equation
[Br:1]Br.[C:3]([C:6]1[C:15]2[O:14][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:12]([CH3:22])[C:11](=[O:23])[C:10]=2[CH:9]=[CH:8][CH:7]=1)(=[O:5])[CH3:4]>C(Cl)(Cl)Cl>[Br:1][CH2:4][C:3]([C:6]1[C:15]2[O:14][C:13]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:12]([CH3:22])[C:11](=[O:23])[C:10]=2[CH:9]=[CH:8][CH:7]=1)=[O:5]

Participants

4

Reactant 2

HCID 24408BromineHCID 22994586HCID 22994586, compound

Product 1

HCID 19972720HCID 19972720, compoundYield 63.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of 11.2 g of bromine in 250 ml of chloroform was added, over a period of two hours at 20°-25° C., to a solution of 19.5 g of Intermediate III in 700 ml of chloroform. After stirring for 1 hour at 20°-25° C., the solution was washed with 400 ml of an aqueous 2N sodium hydroxide solution and then repeatedly with water, dried with anhydrous sodium sulphate and stripped in vacuo. The crude product was treated with diethyl ether, collected by suction filtration and crystallized from acetone, to give 16 g of the title compound, melting point 134°-135° C.

Workup

  1. washthe solution was washed with 400 ml of an aqueous 2N sodium hydroxide solution
  2. dry with materialrepeatedly with water, dried with anhydrous sodium sulphate
  3. additionThe crude product was treated with diethyl ether
  4. filtrationcollected by suction filtration
  5. customcrystallized from acetone

Sources & evidence

ORD record
ord-7074739d95214032aeeaf44835e7f4f4
Source dataset
uspto-grants-1995_09
Patent number
US05453518

Reaction notes

Loading…