Bromine → HCID 66938946, compound

HRID 1257373Notes

Reaction equation

HRID 1257373 reaction equation
[C:1]([O:4][CH2:5][C:6]1[N:7]=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)[S:9][CH:10]=1)(=[O:3])[CH3:2].[Br:21]Br.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(O)(=O)C>[C:1]([O:4][CH2:5][C:6]1[N:7]=[C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:18])([F:19])[F:20])[CH:12]=2)[S:9][C:10]=1[Br:21])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 24408BromineHCID 24477Sodium ThiosulfateHCID 66939415HCID 66939415, compound

Product 1

HCID 66938946HCID 66938946, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Conditions

Temperature
5 °C

Procedure

Under a nitrogen atmosphere at 0° C., to a solution (10 mL) of the crude compound (21 mmol) obtained in Example 64c in acetic acid was slowly added dropwise a solution (10 mL) of bromine (2.5 g, 31 mmol) in acetic acid, and the mixture was stirred at 0-10° C. overnight. An aqueous sodium thiosulfate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The resulting crude title compound was purified by column chromatography (hexane-hexane/ethyl acetate=80/20) to give the title compound (4.0 g, 51%) as a colorless solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe obtained organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customThe resulting crude title compound was purified by column chromatography (hexane-hexane/ethyl acetate=80/20)

Sources & evidence

ORD record
ord-7c75be76bbcc426da08e92cfc9e17e74
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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