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

HRID 1864536Notes

Reaction equation

HRID 1864536 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-fc21b25f99294b71b6328cf2ced2aa5a
Source dataset
uspto-grants-2009_12
Patent number
US07625914B2

Reaction notes

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