2-Chloro-4-fluorophenol → 8-Chloro-4-(2-chloro-4-fluorophenoxy)quinoline

HRID 1885531Notes

Reaction equation

HRID 1885531 reaction equation
Cl[C:2]1[C:11]2[C:6](=[C:7]([Cl:12])[CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[Cl:13][C:14]1[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=1[OH:21]>>[Cl:12][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[N:5]=[CH:4][CH:3]=[C:2]2[O:21][C:15]1[CH:16]=[CH:17][C:18]([F:20])=[CH:19][C:14]=1[Cl:13]

Participants

3

Reactant 2

HCID 748142-Chloro-4-fluorophenolHCID 889734,8-Dichloroquinoline2×

Product 1

HCID 1301978-Chloro-4-(2-chloro-4-fluorophenoxy)quinolineYield 49.5%

Conditions

Temperature
160 °C

Procedure

A mixture of 2.0 g of 4,8-dichloroquinoline and 2.96 g of 2-chloro-4-fluorophenol was heated to 160° C. and stirred. Progress of the reaction was monitored using TLC. When no 4,8-dichloroquinoline remained, the product was washed with base to remove phenol, then purified using HPLC. A brown solid resulted, which was recrystallized in heptane to give 1.54 g of the title product as yellow crystals. Yield: 49%. M.P. 99°-101° C.

Workup

  1. washthe product was washed with base
  2. customto remove phenol
  3. custompurified
  4. customA brown solid resulted
  5. customwhich was recrystallized in heptane

Sources & evidence

ORD record
ord-9d946dfd647946e1ac43b8c7b9d1f994
Source dataset
uspto-grants-1992_09
Patent number
US05145843

Reaction notes

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