Bromine → HCID 19972720, compound

HRID 1452276Notes

Reaction equation

HRID 1452276 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 the Intermediate V in 700 ml of chloroform. After stirring for 1 hour at 20°-25° C., the solution was washed with 400 ml of 2N aqueous sodium hydroxide solution and then repeatedly with water, dried with anhydrous sodium sulfate and stripped in vacuo. The crude product was treated with diethyl ether, collected by suction filtration and crystallized from acetone, yielding 16 g of the title compound, m.p 134°-135° C.

Workup

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

Sources & evidence

ORD record
ord-a4fed3234de34624a294f242f8d98a8d
Source dataset
uspto-grants-1997_02
Patent number
US05605896

Reaction notes

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