Diethyl Ether → 1-(2-Bromopyridin-4-yl)-propan-1-ol

HRID 1423044Notes

Reaction equation

HRID 1423044 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH:8]=[O:9])[CH:5]=[CH:4][N:3]=1.[CH2:10]([Mg]Cl)[CH3:11].CCOCC>C1COCC1>[Br:1][C:2]1[CH:7]=[C:6]([CH:8]([OH:9])[CH2:10][CH3:11])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 27629912-Bromo-4-pyridinecarboxaldehydeHCID 178461633HCID 178461633, compound

Product 1

HCID 866408041-(2-Bromopyridin-4-yl)-propan-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a chilled (−78° C.) solution of 2-bromopyridine-4-carboxaldehyde (7.0 g, 38 mmol) in THF (200 mL) is added a 2 M solution of ethylmagnesium chloride in ether (23.5 mL, 47.0 mmol) over a 10 minute period. After 15 minutes, the mixture is gradually warmed to room temperature over 1 hour. The reaction is quenched by the slow addition of saturated aqueous NH4Cl (100 mL) and extracted with EtOAc (2×200 mL). The combined organic layers are washed with brine, dried over sodium sulfate, filtered and concentrated. The crude material is purified by silica gel chromatography eluting with a gradient of 20-40% EtOAc in hexanes to afford 1-(2-bromopyridin-4-yl)-propan-1-ol.

Workup

  1. customThe reaction is quenched by the slow addition of saturated aqueous NH4Cl (100 mL)
  2. extractionextracted with EtOAc (2×200 mL)
  3. washThe combined organic layers are washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material is purified by silica gel chromatography
  8. washeluting with a gradient of 20-40% EtOAc in hexanes

Sources & evidence

ORD record
ord-be93e4dcde25446ea7882c48c797959d
Source dataset
uspto-grants-2015_01
Patent number
US08927550B2

Reaction notes

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