4-Fluorophenol → HCID 15483748, compound

HRID 1953450Notes

Reaction equation

HRID 1953450 reaction equation
Br[CH2:2][C:3]1[C:12]2[C:7](=[C:8]([Cl:13])[CH:9]=[CH:10][CH:11]=2)[N:6]=[CH:5][CH:4]=1.[H-].[Na+].[F:16][C:17]1[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=1>C1COCC1>[F:16][C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:2][C:3]2[C:12]3[C:7](=[C:8]([Cl:13])[CH:9]=[CH:10][CH:11]=3)[N:6]=[CH:5][CH:4]=2)=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 97324-FluorophenolHCID 24758Sodium hydrideHCID 15483747HCID 15483747, compound

Product 1

HCID 15483748HCID 15483748, compoundYield 51.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Bromomethyl-8-chloroquinoline (0.8 g, 3.11 mmol) was dissolved with stirring in dry THF (10 mls) and sodium hydride (0.15 g, 60% dispersion in mineral oil, 6.23 mmol) added. The mixture was stirred at room temperature for 15 minutes and 4-fluorophenol (0.52 g, 3.11 mmol) added. The mixture was stirred at room temperature overnight and worked up to provide the product (0.46 g, 51.2%) as a white solid, mp 144-5° C.

Workup

  1. stirringThe mixture was stirred at room temperature overnight

Sources & evidence

ORD record
ord-07e9b67d64fa407f94e6ceff82a56e6e
Source dataset
uspto-grants-2000_09
Patent number
US06117884

Reaction notes

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