4-Bromophenol → 2-(4-bromophenoxymethyl)quinoline

HRID 446802Notes

Reaction equation

HRID 446802 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Cl[CH2:10][C:11]1[CH:20]=[CH:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:12]=1.C([O-])([O-])=O.[K+].[K+]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:10][C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:12]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 78084-BromophenolHCID 11430Potassium CarbonateHCID 203942-(Chloromethyl)quinoline

Product 1

HCID 140976052-(4-bromophenoxymethyl)quinolineYield 50.3%

Procedure

To a stirred solution of 4-bromophenol (10 g, 0.057 mol) and 2-(chloro methyl)quinoline (15.4 g, 0.063 mol) in AcN (25 mL) was added K2CO3 (24 g, 0.17 mol). The reaction mixture was refluxed for 3 h, filtered and the filtrate was concentrated in vacuo. The residue was diluted with water and extracted with EtOAc (2×200 mL). The combined organic layers were dried over anhydrous Na2SO4, filtered, and concentrated in vacuo to obtain 2-((4-bromophenoxy)methyl)quinoline (9 g, 50%) as a solid.

Workup

  1. temperatureThe reaction mixture was refluxed for 3 h
  2. filtrationfiltered
  3. concentrationthe filtrate was concentrated in vacuo
  4. additionThe residue was diluted with water
  5. extractionextracted with EtOAc (2×200 mL)
  6. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c0f700be047748e1993a294bf3af7ecf
Source dataset
uspto-grants-2013_07
Patent number
US08481534B2

Reaction notes

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