3-Acetyl-5-bromopyridine → 2-(5-Bromo-3-pyridyl)propan-2-ol

HRID 530011

Reaction equation

HRID 530011 reaction equation
[CH3:1][Mg]Br.[Br:4][C:5]1[CH:6]=[C:7]([C:11](=[O:13])[CH3:12])[CH:8]=[N:9][CH:10]=1>O1CCCC1>[Br:4][C:5]1[CH:6]=[C:7]([C:11]([OH:13])([CH3:1])[CH3:12])[CH:8]=[N:9][CH:10]=1

Participants

4

Reactant 2

HCID 8204233-Acetyl-5-bromopyridineHCID 178418573HCID 178418573, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Methyl magnesium bromide (5.3 mL, 0.075 mol) was added to a stirred solution of 1-(5-bromopyridin-3-yl)ethanone (1.0 g, 0.05 mol) in tetrahydrofuran (20.0 mL), cooled to 0° C. and the resulting mixture was allowed to warm to room temperature and stirred for 1.5 h. The reaction mixture was quenched with 1N hydrochloric acid (20 mL) and extracted with ethyl acetate (2×75 mL). The combined organic layers were dried over sodium sulphate and concentrated under vacuum to afford the crude compound which was purified by column chromatography to obtain 2-(5-bromopyridin-3-yl)propan-2-ol. MS (M+1): 217.1.

Workup

  1. temperatureto warm to room temperature
  2. customThe reaction mixture was quenched with 1N hydrochloric acid (20 mL)
  3. extractionextracted with ethyl acetate (2×75 mL)
  4. dry with materialThe combined organic layers were dried over sodium sulphate
  5. concentrationconcentrated under vacuum
  6. customto afford the crude compound which
  7. customwas purified by column chromatography

Sources & evidence

ORD record
ord-78161fb62e904e78b4b4173b12300011
Source dataset
uspto-grants-2016_05
Patent number
US09351973B2

Linked notes

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