Bromine → HCID 59516832, compound

HRID 1698728Notes

Reaction equation

HRID 1698728 reaction equation
C(=O)([O-])O.[Na+].[Br:6]Br.[CH3:8][O:9][C:10]1[CH:17]=[CH:16][C:13]([CH:14]=[O:15])=[CH:12][C:11]=1[O:18][Si:19]([CH:26]([CH3:28])[CH3:27])([CH:23]([CH3:25])[CH3:24])[CH:20]([CH3:22])[CH3:21].S([O-])([O-])=O.[Na+].[Na+]>C(Cl)(Cl)Cl.ClCCl>[Br:6][C:16]1[CH:17]=[C:10]([O:9][CH3:8])[C:11]([O:18][Si:19]([CH:23]([CH3:25])[CH3:24])([CH:20]([CH3:22])[CH3:21])[CH:26]([CH3:28])[CH3:27])=[CH:12][C:13]=1[CH:14]=[O:15]

Participants

7

Reactant 4

HCID 24408BromineHCID 24437Sodium SulfiteHCID 516892Sodium BicarbonateHCID 86617914HCID 86617914, compound

Product 1

HCID 59516832HCID 59516832, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

After adding 10.9 g of sodium hydrogen carbonate and 2.32 ml of bromine to a solution of 10 g of 4-methoxy-3-triisopropylsilanyloxybenzaldehyde [CAS No. 179260-96-6] in 200 ml of chloroform at 0° C., the mixture was stirred at room temperature for 15 hours. Saturated aqueous sodium sulfite was then added to the reaction mixture, and extraction was performed with dichloromethane. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The desiccating agent was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate-heptane) to give the title compound (11.7 g) as a light yellow oil.

Workup

  1. washThe organic layer was washed with saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationThe desiccating agent was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate-heptane)

Sources & evidence

ORD record
ord-25060501b6cc402cb85b756e5b22e351
Source dataset
uspto-grants-2012_04
Patent number
US08163787B2

Reaction notes

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