2-Fluorophenol → HCID 14097601, compound

HRID 569511Notes

Reaction equation

HRID 569511 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].Cl.Cl[CH2:11][C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=1.[OH-].[K+]>C(O)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH2:11][C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=1

Participants

5

Reactant 3

HCID 97072-FluorophenolHCID 14797Potassium HydroxideHCID 30838232-(Chloromethyl)quinoline hydrochloride

Product 1

HCID 14097601HCID 14097601, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
8 °C

Procedure

To a solution of 2-fluorophenol (7.8 g, 70 mmol) in 20 mL ethanol is added 2-(chloromethyl)quinoline hydrochloride (15.0 g, 70 mmol) followed by a solution of potassium hydroxide (7.86 g, 140 mmol) in 50 mL ethanol. The reaction mixture is refluxed overnight. After filtering while still hot, the reaction mixture is cooled to 8° C. to afford 9.3 g (53%) of brown crystals, m.p. 84°-86° C.

Workup

  1. temperatureThe reaction mixture is refluxed overnight
  2. filtrationAfter filtering while still hot, the reaction mixture

Sources & evidence

ORD record
ord-001cfba669ba4eedaf3c1bab5435b846
Source dataset
uspto-grants-1988_03
Patent number
US04732978

Reaction notes

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