Carbon tetrabromide → HCID 19085566, compound

HRID 962760Notes

Reaction equation

HRID 962760 reaction equation
[C:1]1([CH:7]([O:11][C:12]2[CH:36]=[CH:35][C:15]([C:16]([C:18]3[C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[N:20]([CH2:27][CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH:19]=3)=[O:17])=[CH:14][CH:13]=2)[CH2:8][CH2:9]O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:57].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Br:57][CH2:9][CH2:8][CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[O:11][C:12]1[CH:13]=[CH:14][C:15]([C:16]([C:18]2[C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:20]([CH2:27][CH2:28][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH:19]=2)=[O:17])=[CH:35][CH:36]=1

Participants

6

Reactant 4

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 22435862HCID 22435862, compound

Product 1

HCID 19085566HCID 19085566, compoundYield 87.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ethyl 4-{3-[4-(1-phenyl-3-hydroxypropoxy) benzoyl]indol-1-yl}butanoate (4.00 g) obtained in Step 1 was dissolved in methylene chloride (40 ml). Triphenylphosphine (3.24 g) and carbon tetrabromide (3.24 g) were added to the resultant solution while cooling on ice bath and stirred for 30 minutes at room temperature. Saturated sodium bicarbonate solution was added to the reaction mixture to separate an organic layer. The organic layer was washed with brine and then dried. The solvent was distilled off. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1), obtaining 3.97 g of ethyl 4-{3-[4-(3-bromo-1-phenylpropoxy)benzoyl]indol-1-yl}butanoate as colorless oily substance.

Workup

  1. temperaturewhile cooling on ice bath
  2. customto separate an organic layer
  3. washThe organic layer was washed with brine
  4. customdried
  5. distillationThe solvent was distilled off
  6. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-bcabffeacd2f4bfebe294512224ddfa4
Source dataset
uspto-grants-1998_06
Patent number
US05760040

Reaction notes

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