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

HRID 971096Notes

Reaction equation

HRID 971096 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 (4 ml, 12 mmol) in ether. The resulting slurry was then 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 then 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-03cd0092b09d46b09266286a952da0d4
Source dataset
uspto-grants-2007_12
Patent number
US07312334B2

Reaction notes

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