2-Chloro-7-fluoroquinoline-3-carbaldehyde → 1-(2-Chloro-7-fluoroquinolin-3-yl)ethanol

HRID 1019793Notes

Reaction equation

HRID 1019793 reaction equation
[Cl:1][C:2]1[C:11]([CH:12]=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][C:6]([F:14])=[CH:7][CH:8]=2)[N:3]=1.[CH3:15][Mg+].[Br-]>C1COCC1>[Cl:1][C:2]1[C:11]([CH:12]([OH:13])[CH3:15])=[CH:10][C:9]2[C:4](=[CH:5][C:6]([F:14])=[CH:7][CH:8]=2)[N:3]=1

Participants

4

Reactant 2

HCID 120991792-Chloro-7-fluoroquinoline-3-carbaldehydeHCID 178418689HCID 178418689, compound

Product 1

HCID 242760771-(2-Chloro-7-fluoroquinolin-3-yl)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 2-chloro-7-fluoroquinoline-3-carbaldehyde (44.7 g, 213 mmol) in THF (600 mL) was treated with MeMgBr (78.0 mL, 234 mmol 1.1 eq) at −20° C. After stirring overnight, the reaction was quenched with NH4Cl solution and extracted with Et2O (300 mL and 100 mL). The organic layers were washed with water, brine, dried over Na2SO4, concentrated and recrystallized from EtOAc (100 mL) and hexane (1 L). A pale yellow solid of 1-(2-chloro-7-fluoroquinolin-3-yl)-ethanol was obtained (41 g, 85%). Mass Spectrum (ESI) m/e=226 (M+1).

Workup

  1. customthe reaction was quenched with NH4Cl solution
  2. extractionextracted with Et2O (300 mL and 100 mL)
  3. washThe organic layers were washed with water, brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customrecrystallized from EtOAc (100 mL) and hexane (1 L)

Sources & evidence

ORD record
ord-da16a28943044505b76803b6d18524d3
Source dataset
uspto-grants-2014_05
Patent number
US08716290B2

Reaction notes

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