5-Bromo-2-fluoro-3-pyridinecarboxaldehyde → 1-(5-Bromo-2-fluoropyridin-3-yl)ethan-1-ol

HRID 627645Notes

Reaction equation

HRID 627645 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([F:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH3:11][Mg]Br>C1COCC1>[Br:1][C:2]1[CH:9]=[C:6]([CH:7]([OH:8])[CH3:11])[C:5]([F:10])=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 454801925-Bromo-2-fluoro-3-pyridinecarboxaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 426090481-(5-Bromo-2-fluoropyridin-3-yl)ethan-1-olYield 100.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-bromo-2-fluoronicotinaldehyde (10 g, 49 mmol) in THF (100 mL) at −78° C. was added dropwise methylmagnesium bromide (3.0 M solution in diethyl ether, 24.5 mL, 73.5 mmol). After the addition, the reaction was warmed to room temperature and stirred for 17 h. The mixture was carefully quenched with saturated ammonium chloride and extracted with EtOAc. The combined organic extracts were washed with brine, dried over Na2SO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (eluted with 0-10% EtOAc/hexanes) gave 1-(5-bromo-2-fluoropyridin-3-yl)ethanol (10.8 g, 49.1 mmol, 100% yield) as a yellow oil. LC/MS (ESI+) m/z=220 (M+H).

Workup

  1. additionAfter the addition
  2. customThe mixture was carefully quenched with saturated ammonium chloride
  3. extractionextracted with EtOAc
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by flash column chromatography on silica gel (eluted with 0-10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-000a14158f3a4d898529453c67611717
Source dataset
uspto-grants-2016_04
Patent number
US09309263B2

Reaction notes

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