1,4-Dibromobutane → HCID 13772345, compound

HRID 1638983Notes

Reaction equation

HRID 1638983 reaction equation
[CH2:1]([C:8]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[OH:25])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([CH3:17])[C:9]1=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[Br:32][CH2:33][CH2:34][CH2:35][CH2:36]Br>CC(=O)CC>[CH2:1]([C:8]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[O:25][CH2:36][CH2:35][CH2:34][CH2:33][Br:32])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]([CH3:17])[C:9]1=[O:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 13772343HCID 13772343, compound

Product 1

HCID 13772345HCID 13772345, compoundYield 83.1%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

16.5 g (0.05 mol) of 3-benzyl-3-(2-hydroxyphenyl)-1- methylindolin-2-one in 250 ml of 2-butanone are stirred under reflux with 20.7 g (0.15 mol) of ground anhydrous potassium carbonate and 17.2 ml (0.15 mol) of 1,4-dibromobutane for 5 hours. The hot mixture is filtered with suction, and the filtrate is concentrated in vacuo. The crystalline residue is triturated with petroleum ether, and the product is isolated after removal of the solvent with suction. 19.3 g of product of melting point 174°-5° C. are obtained.

Workup

  1. filtrationThe hot mixture is filtered with suction
  2. concentrationthe filtrate is concentrated in vacuo
  3. customThe crystalline residue is triturated with petroleum ether
  4. customthe product is isolated
  5. customafter removal of the solvent with suction

Sources & evidence

ORD record
ord-14c5bff02ae84c4699bfa864ff4e797c
Source dataset
uspto-grants-1989_11
Patent number
US04882329

Reaction notes

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