5-Bromo-3-pyridinecarboxaldehyde → 3-Bromo-5-(1-hydroxyethyl)pyridine

HRID 2277693Notes

Reaction equation

HRID 2277693 reaction equation
[CH3:1][Mg]Br.[Br:4][C:5]1[CH:6]=[C:7]([CH:11]=[O:12])[CH:8]=[N:9][CH:10]=1>C1COCC1>[Br:4][C:5]1[CH:6]=[C:7]([CH:11]([OH:12])[CH3:1])[CH:8]=[N:9][CH:10]=1

Participants

4

Reactant 2

HCID 27847345-Bromo-3-pyridinecarboxaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 129974353-Bromo-5-(1-hydroxyethyl)pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Methylmagnesium bromide (1M in THF, 12 mL, 12 mmol) was added dropwise to a solution of 5-bromo-pyridine-3-carbaldehyde (1.85, 10 mmol) in dry THF (20 mL) at −78° C. The resulting mixture was slowly warmed up to 0° C. during a 2 hour period and then quenched by aq. satd. NH4Cl solution. After extraction with DCM, the organic layer was washed with brine, dried over anhy. Na2SO4, filtered and concentrated in vacuo to give title compound as a crude product (1.9 g, 98%).

Workup

  1. customquenched by aq. satd
  2. extractionAfter extraction with DCM
  3. washthe organic layer was washed with brine
  4. customdried over anhy
  5. filtrationNa2SO4, filtered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a5ca48bf633949e3ae3066647da4b8e0
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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