Diethyl Ether → 2-(5-Bromo-3-pyridyl)propan-2-ol

HRID 351739

Reaction equation

HRID 351739 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:12]=1)C(OCC)=O.[CH3:13][Mg]Br.C([O:18][CH2:19][CH3:20])C>>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:19]([OH:18])([CH3:20])[CH3:13])[CH:12]=1

Participants

4

Reactant 3

HCID 3283Diethyl Ether2×HCID 140785Ethyl 5-bromopyridine-3-carboxylateHCID 178418573HCID 178418573, compound

Product 1

HCID 223919662-(5-Bromo-3-pyridyl)propan-2-ol

Procedure

To a solution of ethyl 5-bromonicotinate (1.02 g, 4.4 mmol) in diethyl ether (15 mL) at −30° C. was added a 3M solution of methyl magnesium bromide in ether (4 mL, 12 mmol). The resulting slurry was refluxed for 2 hours then cooled and quenched with an excess of 0.5M aqueous monobasic sodium phosphate and partitioned between ether and water. The product from the organic phase was chromatographed on silica gel eluting with a 2:1:2 mixture of ether, pentane and ammonia-saturated methylene chloride to afford the 3-bromo-5-(1-hydroxy-1-methylethyl)pyridine compound as a yellow oil.

Workup

  1. temperatureThe resulting slurry was refluxed for 2 hours
  2. temperaturethen cooled
  3. customquenched with an excess of 0.5M aqueous monobasic sodium phosphate
  4. custompartitioned between ether and water
  5. customThe product from the organic phase was chromatographed on silica gel eluting with a 2:1:2 mixture of ether, pentane and ammonia-saturated methylene chloride

Sources & evidence

ORD record
ord-3f904e1c57c549b3b6f2c03ccbbd8aab
Source dataset
uspto-grants-2004_06
Patent number
US06743802B2

Linked notes

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