Water → (5-Bromopyridin-2-yl)methanol

HRID 2170033Notes

Reaction equation

HRID 2170033 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]=[O:9])=[N:6][CH:7]=1.[BH4-].[Na+].O>C(O)C.C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][OH:9])=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 98775625-Bromopyridine-2-carbaldehyde

Product 1

HCID 5200169(5-Bromopyridin-2-yl)methanolYield 95.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-bromopyridine-2-carbaldehyde (5.00 g, 26.9 mmol) dissolved in a mixture of ethanol (75 mL) and THF (25 mL) was added sodium borohydride (0.407 g, 10.8 mmol) in small portions. After 45 minutes 0.5 mL water was added and the mixture and evaporated to dryness. The oily residue was subjected to flash chromatography (silica, EtOAc/EtOH/Et3N 90:5:5) to give (5-bromo-pyridin-2-yl)-methanol (4.81 g, 86%) as pale-yellow oil.

Workup

  1. customthe mixture and evaporated to dryness

Sources & evidence

ORD record
ord-305aefc1cdb74978881850ffeb49f78f
Source dataset
uspto-grants-2015_06
Patent number
US09050327B2

Reaction notes

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