6-Bromo-3-pyridinecarboxaldehyde → HCID 86640808, compound

HRID 1423059Notes

Reaction equation

HRID 1423059 reaction equation
[Br:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]=[O:9])=[CH:4][CH:3]=1.[CH2:10]([Mg]Cl)[CH3:11]>C1COCC1.[Cl-].[NH4+]>[Br:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]([OH:9])[CH2:10][CH3:11])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 117692346-Bromo-3-pyridinecarboxaldehydeHCID 178461633HCID 178461633, compound

Product 1

HCID 86640808HCID 86640808, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolvent

Procedure

To a chilled (0° C.) solution of 6-bromopyridine-3-carboxaldehyde (15.0 g, 80.6 mmol) in a 1:1 mixture of ether-toluene (400 mL) is added a 2 M solution of ethylmagnesium chloride (40.0 mL, 80.0 mmol) in THF over a 15 minute period. After 4 hours, the mixture is diluted with saturated aqueous ammonium chloride (300 mL) and the organic layer is separated. The aqueous layer is extracted with EtOAc (2×100 mL). The combined organic layers are washed with brine (2×50 mL), dried over magnesium sulfate, filtered and concentrated. The crude material is passed through a pad of silica gel eluting with dichloromethane-hexanes (0-100%). The material from the pad is purified by silica gel chromatography eluting with EtOAc-hexanes (2:98, then 4:96, then 6:94, then 8:92, then 1:9, then 12:88, then 15:85) to afford 1-(6-bromopyridin-3-yl)-propan-1-ol as an oil.

Workup

  1. customthe organic layer is separated
  2. extractionThe aqueous layer is extracted with EtOAc (2×100 mL)
  3. washThe combined organic layers are washed with brine (2×50 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe material from the pad is purified by silica gel chromatography
  8. washeluting with EtOAc-hexanes (2:98

Sources & evidence

ORD record
ord-b8e289f779f24deeb12dfe2e859a98ce
Source dataset
uspto-grants-2015_01
Patent number
US08927550B2

Reaction notes

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