Ethyl 5-bromopyridine-3-carboxylate → (5-Bromo-3-pyridinyl)methanol

HRID 910284Notes

Reaction equation

HRID 910284 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:12]=1)[C:7](OCC)=[O:8].[BH4-].[Na+]>CO>[Br:1][C:2]1[CH:12]=[C:6]([CH2:7][OH:8])[CH:5]=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 140785Ethyl 5-bromopyridine-3-carboxylateHCID 4311764Sodium borohydride

Product 1

HCID 2784733(5-Bromo-3-pyridinyl)methanolYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A solution of 9 g (40 mmol) of ethyl 5-bromonicotinate in 25 ml of methanol is added dropwise, at room temperature, to a suspension of 14.8 g (400 mmol) of sodium borohydride in 75 ml of methanol. After addition, the reaction medium is refluxed for 2 hours. The reaction medium is evaporated to dryness, taken up in aqueous sodium hydroxide solution to pH 9, and extracted with ethyl acetate. The organic phase is dried over magnesium sulfate, filtered and evaporated under vacuum. 3.7 g (50%) of (5-bromopyrid-3-yl)methanol are obtained.

Workup

  1. additionAfter addition
  2. temperaturethe reaction medium is refluxed for 2 hours
  3. customThe reaction medium is evaporated to dryness
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic phase is dried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated under vacuum

Sources & evidence

ORD record
ord-49d48d2bdbf5421bba144862e504a0e4
Source dataset
uspto-grants-2011_09
Patent number
US08022079B2

Reaction notes

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