Water → 2-(6-Bromopyridin-2-yl)propan-2-ol

HRID 385754Notes

Reaction equation

HRID 385754 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:4][CH:3]=1.[CH3:11][Mg]Br.O>C(OCC)C>[Br:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])([CH3:11])[CH3:9])[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 112985782-Acetyl-6-bromopyridineHCID 178418573HCID 178418573, compound

Product 1

HCID 227143012-(6-Bromopyridin-2-yl)propan-2-ol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 1-(6-bromopyridin-2-yl)ethanone (5 g, 25.0 mmol) in diethyl ether (77 mL) at 0° C. was treated with methyl magnesium bromide (8.33 mL, 25.0 mmol). After 3 hours, water was added to quench the excess methyl magnesium bromide, and then concentrated aqueous hydrogen chloride solution was added until two layers were obtained. The layers were separated and the aqueous layer was extracted with diethyl ether (3×50 mL) The combined organic layers were dried over sodium sulfate, filtered, and concentrated to yield the title compound.

Workup

  1. customto quench the excess methyl magnesium bromide
  2. additionconcentrated aqueous hydrogen chloride solution was added until two layers
  3. customwere obtained
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with diethyl ether (3×50 mL) The combined organic layers
  6. dry with materialwere dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-3e5fe060ab8f4f1fba1391a7720750e2
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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