1-(5-Bromopyridin-2-yl)ethan-1-one → 2-(5-Bromopyridin-2-yl)propan-2-ol

HRID 510991Notes

Reaction equation

HRID 510991 reaction equation
[CH3:1][Mg]Cl.[Br:4][C:5]1[CH:6]=[CH:7][C:8]([C:11](=[O:13])[CH3:12])=[N:9][CH:10]=1>C1COCC1>[Br:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]([OH:13])([CH3:1])[CH3:12])=[N:9][CH:10]=1

Participants

4

Reactant 2

HCID 231453451-(5-Bromopyridin-2-yl)ethan-1-oneHCID 178418332HCID 178418332, compound

Product 1

HCID 154863922-(5-Bromopyridin-2-yl)propan-2-olYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3.0 M Methylmagnesium chloride in THF (0.3 mL) was added dropwise to a mixture of 1-(5-bromopyridin-2-yl)ethanone (100 mg, 0.5 mmol) in THF (10 mL) at 0° C. After stirring for 1 h at room temperature, the reaction was quenched with 1 N NH4Cl and was extracted with EtOAc. The combined organic layer was washed with brine and dried over MgSO4, concentrated to give crude product (0.1 g, 100%). Crude was used in next step without purification. LCMS calculated for C8H11BrNO (M+H)+: m/z=215.9, 217.9. found: 215.8, 217.8.

Workup

  1. customthe reaction was quenched with 1 N NH4Cl
  2. extractionwas extracted with EtOAc
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1134f33e71524093a69900d8a541cb67
Source dataset
uspto-grants-2015_08
Patent number
US09096600B2

Reaction notes

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