Benzyl Bromide → HCID 53706852, compound

HRID 653146Notes

Reaction equation

HRID 653146 reaction equation
[CH3:1][O:2][C:3]([C:5]1[N:6]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:7]2[C:12]([C:13]=1[OH:14])=[CH:11][C:10]([O:15][CH3:16])=[CH:9][CH:8]=2)=[O:4].C(=O)([O-])[O-].[K+].[K+].[CH2:29](Br)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>CC(C)=O>[CH3:1][O:2][C:3]([C:5]1[N:6]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:7]2[C:12]([C:13]=1[O:14][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[CH:11][C:10]([O:15][CH3:16])=[CH:9][CH:8]=2)=[O:4]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 54696100Methyl 3-hydroxy-5-methoxy-1-phenyl-1H-indole-2-carboxylate

Product 1

HCID 53706852HCID 53706852, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 155 g (0.52 mole) of 3-hydroxy-5-methoxy-1-phenyl-1H-indole-2-carboxylic acid methyl ester [P. C. Unangst and M. E. Carethers, J. Heterocyclic Chem., 21, 709 (1984)], 83.0 g (0.60 mole) of anhydrous potassium carbonate, and 68 ml (97.8 g; 0.57 mole) of benzyl bromide in 2250 ml of acetone was stirred at reflux for 20 hours. The mixture was cooled, filtered, and the filter cake was washed several times with fresh acetone. The combined filtrates were evaporated (vacuum) to yield a crude residue of 5-methoxy-1-phenyl-3-(phenylmethoxy)-1H-indole-2-carboxylic acid methyl ester.

Workup

  1. temperatureat reflux for 20 hours
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. washthe filter cake was washed several times with fresh acetone
  5. customThe combined filtrates were evaporated (vacuum)

Sources & evidence

ORD record
ord-7699f9668ffe4678878b6c76f0854ddb
Source dataset
uspto-grants-1987_06
Patent number
US04675332

Reaction notes

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