Bromine → HCID 67422209, compound

HRID 1799179Notes

Reaction equation

HRID 1799179 reaction equation
[Br:1]Br.[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:12]2[CH:13]=[N:14][C:15]([NH:18][CH3:19])=[CH:16][CH:17]=2)=[O:11])=[CH:6][CH:5]=1.C([O-])(O)=O.[Na+]>C(O)(=O)C>[Br:1][C:16]1[CH:17]=[C:12]([C:10]([C:7]2[CH:6]=[CH:5][C:4]([Cl:3])=[CH:9][CH:8]=2)=[O:11])[CH:13]=[N:14][C:15]=1[NH:18][CH3:19]

Participants

5

Reactant 3

HCID 24408BromineHCID 516892Sodium BicarbonateHCID 67421372HCID 67421372, compound

Product 1

HCID 67422209HCID 67422209, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of bromine (2.29 mL, 44.70 mmol) in acetic acid (30 mL) was added to a solution of compound C (11.0 g, 44.7 mmol) in acetic acid (80 mL) at RT. The mixture was stirred for 1 h, neutralized by the addition of saturated NaHCO3 solution and extracted with ethyl acetate (200 mL). The organic layer was washed with 10% sodium thiosulfate solution, water and brine. The organic layer was dried (Na2SO4), filtered and evaporated. The crude product was purified using column chromatography to obtain 9.0 g (62%) of compound D as viscous light yellow colored oil.

Workup

  1. extractionextracted with ethyl acetate (200 mL)
  2. washThe organic layer was washed with 10% sodium thiosulfate solution, water and brine
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product was purified

Sources & evidence

ORD record
ord-c73e0c26bb24427d8f5d9156b15dd80b
Source dataset
uspto-grants-2013_01
Patent number
US08343996B2

Reaction notes

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