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

HRID 860997Notes

Reaction equation

HRID 860997 reaction equation
C(OC(=O)[C:5]1[CH:10]=[C:9]([Br:11])[CH:8]=[N:7][CH:6]=1)C.[CH3:13][Mg+].[Br-].CC[O:18][CH2:19][CH3:20]>>[Br:11][C:9]1[CH:10]=[C:5]([C:19]([OH:18])([CH3:20])[CH3:13])[CH:6]=[N:7][CH:8]=1

Participants

4

Reactant 3

HCID 3283Diethyl EtherHCID 140785Ethyl 5-bromopyridine-3-carboxylateHCID 178418689HCID 178418689, compound

Product 1

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

Procedure

To a solution of 5-bromo-nicotinic acid ethyl ester (1.0 eq.) in Et2O (0.3M) at −30° C. was added MeMgBr (2.7 eq.; 3M in Et2O). The mixture was refluxed for 2 h, poured in 0.5M aqueous NaH2PO4 and extracted with Et2O (2×). The combined organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated. Flash chromatography (Hex:Et2O:CH2Cl2; 2:1:2) afforded the title compound as a yellow oil.

Workup

  1. temperatureThe mixture was refluxed for 2 h
  2. extractionextracted with Et2O (2×)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-12b3fc05a2e8460e9f60eaa394c72e0f
Source dataset
uspto-grants-2006_12
Patent number
US07153968B2

Reaction notes

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