Dimethylformamide → HCID 87780782, compound

HRID 2115155Notes

Reaction equation

HRID 2115155 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH:8]2[CH2:13][CH2:12][CH:11]([CH:14]3[CH2:19][CH2:18][CH:17]([CH2:20][CH2:21][CH3:22])[CH2:16][CH2:15]3)[CH2:10][CH2:9]2)[CH:5]=[CH:4][C:3]=1O.[C:24](=[O:27])([O-])[O-].[K+].[K+].[CH2:30](Cl)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.CN(C=O)C>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[Br:1][C:2]1[CH:7]=[C:6]([CH:8]2[CH2:9][CH2:10][CH:11]([CH:14]3[CH2:15][CH2:16][CH:17]([CH2:20][CH2:21][CH3:22])[CH2:18][CH2:19]3)[CH2:12][CH2:13]2)[CH:5]=[CH:4][C:3]=1[CH:30]([O:27][CH:24]([C:3]1[CH:4]=[CH:5][C:6]([CH:8]2[CH2:9][CH2:10][CH:11]([CH:14]3[CH2:19][CH2:18][CH:17]([CH2:20][CH2:21][CH3:22])[CH2:16][CH2:15]3)[CH2:12][CH2:13]2)=[CH:7][C:2]=1[Br:1])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 69316420HCID 69316420, compound

Product 1

HCID 87780782HCID 87780782, compoundYield 148.3%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolvent

Procedure

The foregoing 2-bromo-4-(4-(4-propylcyclohexyl)cyclohexyl)phenol (250 mg), potassium carbonate (109 mg), and benzyl chloride (135 mg) were mixed, to which were then added DMF (2 ml) and tetrabutylammonium bromide (20 mg), and the mixture was refluxed by heating for 30 minutes. After completion of the reaction, the reaction mixture was added in water and extracted with toluene. The resulting toluene layer was washed with water, rinsed with a sodium hydrogencarbonate aqueous solution, and then dried over anhydrous magnesium sulfate. The solution was concentrated in vacuo and then subjected to isolation and purification by silica gel column chromatography, thereby obtaining a colorless crystal (300 mg) of 2-bromo-4-(4-(4-propylcyclohexyl)cyclohexyl)phenylbenzyl ether.

Workup

  1. temperatureby heating for 30 minutes
  2. customAfter completion of the reaction
  3. extractionextracted with toluene
  4. washThe resulting toluene layer was washed with water
  5. washrinsed with a sodium hydrogencarbonate aqueous solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationThe solution was concentrated in vacuo
  8. customsubjected to isolation and purification by silica gel column chromatography

Sources & evidence

ORD record
ord-a4e77ca5034c483db80591e1a6a67b86
Source dataset
uspto-grants-2008_10
Patent number
US07435455B2

Reaction notes

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