Ammonium Chloride → 1-(6-bromopyridin-2-yl)ethanol

HRID 545250Notes

Reaction equation

HRID 545250 reaction equation
[BH4-].[Na+].[C:3]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([Br:12])[N:7]=1)(=[O:5])[CH3:4].[Cl-].[NH4+]>C(O)C>[Br:12][C:8]1[N:7]=[C:6]([CH:3]([OH:5])[CH3:4])[CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 112985782-Acetyl-6-bromopyridine

Product 1

HCID 110634791-(6-bromopyridin-2-yl)ethanolYield 100.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

With cooling with ice, 426 mg of sodium borohydride was added to ethanol (50 mL) solution of 4.50 g of 2-acetyl-6-bromopyridine. After stirred for 1 hour, aqueous saturated ammonium chloride solution was added to the reaction liquid, extracted with ethyl acetate, washed with saturated saline water, and dried with anhydrous magnesium sulfate. After concentrated under reduced pressure, 4.58 g of the entitled compound was obtained as a colorless oily substance.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with saturated saline water
  3. dry with materialdried with anhydrous magnesium sulfate
  4. concentrationAfter concentrated under reduced pressure

Sources & evidence

ORD record
ord-0473f1e63db4488d879b1076ef22b2cb
Source dataset
uspto-grants-2011_05
Patent number
US07935708B2

Reaction notes

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