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

HRID 2175240Notes

Reaction equation

HRID 2175240 reaction equation
[BH4-].[Na+].[Br:3][C:4]1[CH:5]=[CH:6][C:7]([C:10](OCC)=[O:11])=[N:8][CH:9]=1>CO>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][OH:11])=[N:8][CH:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 12686158Ethyl 5-bromopicolinate

Product 1

HCID 5200169(5-Bromopyridin-2-yl)methanolYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of NaBH4 (0.822 g, 21.73 mmol) in MeOH (25 mL) was added ethyl 5-bromopicolinate (1.0 g, 4.35 mmol) portion-wise over a period of 10 min at room temperature. The mixture was stirred at room temperature for 10 min and then heated to 70° C. for 30 min. The solvent was removed in vacuo, and the resulting residue was diluted with EtOAc and water. The aqueous phase was adjusted to pH 7 with 1 N aq. HCl, and extracted with EtOAc. The combined organic layer was dried over MgSO4, filtered, and concentrated in vacuo to afford the title compound (0.65 g, 80% yield) as a white solid. LCMS, [M+H]+=187.9.

Workup

  1. temperatureheated to 70° C. for 30 min
  2. customThe solvent was removed in vacuo
  3. additionthe resulting residue was diluted with EtOAc and water
  4. extractionextracted with EtOAc
  5. dry with materialThe combined organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-be7824b77be74e21a356cd55e420f277
Source dataset
uspto-grants-2015_06
Patent number
US09062028B2

Reaction notes

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