Sodium borohydride → (5-Bromopyridin-2-yl)methanol

HRID 578750Notes

Reaction equation

HRID 578750 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8](OC)=[O:9])=[N:6][CH:7]=1.[BH4-].[Na+]>C(O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][OH:9])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 7016458Methyl 5-bromopyridine-2-carboxylate

Product 1

HCID 5200169(5-Bromopyridin-2-yl)methanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methyl 5-bromopyridine-2-carboxylate (2.00 g, 9.27 mmol) was dissolved in ethanol (20.0 mL). Sodium borohydride (1.05 g, 27.8 mmol) was added at 0° C., and the mixture was stirred at room temperature for 18 h. The mixture was then concentrated under reduced pressure, quenched with 1 N hydrochloric acid, neutralized with solid potassium carbonate and extracted with dichloromethane. The organic layer was dried over magnesium sulfate and evaporated to give 1.57 g (90% of th.) of the title compound.

Workup

  1. concentrationThe mixture was then concentrated under reduced pressure
  2. customquenched with 1 N hydrochloric acid
  3. extractionextracted with dichloromethane
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-da26f20938424b4e8d715b0b9da26a96
Source dataset
uspto-grants-2015_05
Patent number
US09040691B2

Reaction notes

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