Carbon tetrabromide → HCID 22731440, compound

HRID 2085552Notes

Reaction equation

HRID 2085552 reaction equation
[C:1]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([S:15]([C:18]1[C:23]([CH3:24])=[CH:22][C:21]([CH3:25])=[CH:20][C:19]=1[CH3:26])(=[O:17])=[O:16])[CH:10]=[C:9]2[CH3:27])(OCC)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:54]>C1COCC1.C(OCC)(=O)C>[Br:54][CH2:1][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([S:15]([C:18]1[C:23]([CH3:24])=[CH:22][C:21]([CH3:25])=[CH:20][C:19]=1[CH3:26])(=[O:17])=[O:16])[CH:10]=[C:9]2[CH3:27]

Participants

7

Reactant 4

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 21226445Aluminium lithium hydrideHCID 22731441HCID 22731441, compound

Product 1

HCID 22731440HCID 22731440, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Under cooling with ice, 5-carboethoxy-3-methyl-1-(2,4,6-trimethylbenzenesulfonyl)indole (1.13 g, 2.94 mmol) was added to a solution of lithium aluminum hydride (223 mg, 5.88 mmol) in THF (10 ml), followed by stirring for 1 hour. The reaction mixture was mixed with ethyl acetate and a 2N aqueous HCl solution and extracted with chloroform. The organic layer was washed with water and saturated brine, dried over magnesium sulfate and evaporated to remove the solvent. The thus obtained residue was dissolved in methylene chloride (20 ml) and mixed with triphenylphosphine (1.06 g, 4.04 mmol) and carbon tetrabromide (1.34 g, 4.04 mmol) under cooling with ice, followed by stirring for 1 hour. The reaction mixture was evaporated to remove the solvent; the thus obtained residue was subjected to silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:5) to give the titled compound (1.12 g, 94%).

Workup

  1. extractiona 2N aqueous HCl solution and extracted with chloroform
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customto remove the solvent
  6. dissolutionThe thus obtained residue was dissolved in methylene chloride (20 ml)
  7. temperatureunder cooling with ice
  8. stirringby stirring for 1 hour
  9. customThe reaction mixture was evaporated
  10. customto remove the solvent

Sources & evidence

ORD record
ord-62a9a3be3b42444690d5818376f8196c
Source dataset
uspto-grants-2004_04
Patent number
US06720433B2

Reaction notes

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