Diethyl Ether → 2-(5-Bromo-3-pyridyl)propan-2-ol

HRID 1623512Notes

Reaction equation

HRID 1623512 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)C(Cl)=O.[CH3:11][Mg]Br.C([O:16][CH2:17][CH3:18])C>C1COCC1>[Br:1][C:2]1[CH:10]=[C:6]([C:17]([OH:16])([CH3:18])[CH3:11])[CH:5]=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 27812235-Bromonicotinoyl chlorideHCID 178418573HCID 178418573, compound

Product 1

HCID 223919662-(5-Bromo-3-pyridyl)propan-2-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-bromo-nicotinoyl chloride (900 mg, 4.1 mmol) in THF (18 mL) at −78° C. was added a 3.0 M solution of methylmagnesium bromide in diethyl ether (5.44 mL, 16.3 mmol). The reaction was stirred for 20 minutes and then quenched with saturated aqueous ammonium chloride. The reaction was then brought to room temperature, diluted with brine and ethyl acetate and the layers were separated. The aqueous layer was extracted two additional times with ethyl acetate, and the organic layers were combined, dried over anhydrous sodium sulfate, filtered, and concentrated. The resulting residue was purified by silica gel flash chromatography (ethyl acetate-heptane, 0 to 100%) to afford 2-(5-bromo-pyridin-3-yl)-propan-2-ol; MS: (ES+) m/z 216.0 (M+H)+.

Workup

  1. customquenched with saturated aqueous ammonium chloride
  2. customwas then brought to room temperature
  3. additiondiluted with brine and ethyl acetate
  4. customthe layers were separated
  5. extractionThe aqueous layer was extracted two additional times with ethyl acetate
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe resulting residue was purified by silica gel flash chromatography (ethyl acetate-heptane, 0 to 100%)

Sources & evidence

ORD record
ord-3b903d62dc5c4b52990f519f2c423e80
Source dataset
uspto-grants-2014_07
Patent number
US08778972B2

Reaction notes

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