Methanol → HCID 43340411, compound

HRID 2067700Notes

Reaction equation

HRID 2067700 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.C(Cl)Cl.[CH3:14][OH:15]>[Ti](Cl)(Cl)(Cl)Cl.O>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[C:14](=[O:15])[CH2:5][C:4]1[CH:8]=[CH:9][CH:10]=[CH:2][CH:3]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 6344Dichloromethane2×HCID 249055-Bromoindole

Product 1

HCID 43340411HCID 43340411, compound

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 962WaterSolvent

Procedure

To 5-bromoindole (160 g), 1-phenylacetyl-1H-1,2,3-benzotriazole (193.62 g) and methylene chloride (2120 ml) were added, the mixture was stirred under ice cooling while adding a solution of titanium(IV) chloride (179 ml) in a methylene chloride solution (450 ml) and the mixture was stirred at room temperature for 1.5 hours. To the reaction solution, methanol (220 ml) and water (1126 ml) were added, the mixture was stirred at room temperature for 21 hours and in an ice water bath for 3 hours, then the precipitated crystals were obtained by filtration to afford the above-identified compound (163.0 g).

Workup

  1. stirringthe mixture was stirred at room temperature for 1.5 hours
  2. stirringthe mixture was stirred at room temperature for 21 hours and in an ice water bath for 3 hours
  3. customthe precipitated crystals were obtained by filtration

Sources & evidence

ORD record
ord-c9e392e4dd0649cfa1e8b04d73b51a64
Source dataset
uspto-grants-2012_10
Patent number
US08293781B2

Reaction notes

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