Ammonium Chloride → HCID 86667924, compound

HRID 571681Notes

Reaction equation

HRID 571681 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH:8]=[O:9])[C:5]([Cl:10])=[CH:4][CH:3]=1.[CH3:11][Mg]Br.[Cl-].[NH4+]>C1COCC1>[Br:1][C:2]1[N:7]=[C:6]([CH:8]([OH:9])[CH3:11])[C:5]([Cl:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 722123126-Bromo-3-chloro-2-pyridinecarboxaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 86667924HCID 86667924, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-bromo-3-chloropicolinaldehyde (10.0 g, 45.45 mmol) in 200 mL THF stirring at −78° C. under N2 was slowly added methylmagnesium bromide (3.0 M in diethyl ether, 16.63 mL, 50 mmol). The reaction was stirred at this temperature for 3 hours, and then saturated ammonium chloride was added. The mixture was extracted with EtOAc. The combined organic layers were dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (0-1% EtOAc/hexanes over 20 minutes) to provide 1-(6-bromo-3-chloropyridin-2-yl)ethanol (8.4 g, 78%).

Workup

  1. customat −78° C.
  2. extractionThe mixture was extracted with EtOAc
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography (0-1% EtOAc/hexanes over 20 minutes)

Sources & evidence

ORD record
ord-1c6f50ce7e4a4c31a1879522a424579f
Source dataset
uspto-grants-2015_05
Patent number
US09029362B2

Reaction notes

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