Magnesium perchlorate → Methyl 2-bromo-2-(pyridin-2-yl)propanoate

HRID 2203306Notes

Reaction equation

HRID 2203306 reaction equation
Cl([O-])(=O)(=O)=O.[Mg+2].Cl([O-])(=O)(=O)=O.[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH:18]([CH3:23])[C:19]([O:21][CH3:22])=[O:20].[Br:24]N1C(=O)CCC1=O>C(#N)C>[Br:24][C:18]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][N:12]=1)([CH3:23])[C:19]([O:21][CH3:22])=[O:20]

Participants

5

Reactant 3

HCID 24840Magnesium perchlorateHCID 67184N-bromobutanimideHCID 54595201Methyl 2-(pyridin-2-yl)propanoate

Product 1

HCID 67991933Methyl 2-bromo-2-(pyridin-2-yl)propanoate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Magnesium perchlorate (0.46 g, 2.08 mmol) was added to an acetonitrile (18 mL) solution containing the intermediate from Step A (1.04 g, 6.30 mmol). After stirring for 5 minutes N-bromosuccinimide (1.35 g, 7.55 mmol) was added and the reaction solution was stirred overnight. The solution was then partitioned between EtOAc and 1N NaHCO3 aq. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified by silica gel chromatography using a hexanes/EtOAc gradient to give the indicated product. 1H NMR (400 MHz, CH3CN-d3): δ 8.48 (d, J=4.8 Hz, 1H); 7.85-736 (m, 2H); 7.32-7.26 (m, 1H); 3.72 (s, 3H); 2.24 (s, 3H). m/z=244.4 (M+H).

Workup

  1. additionwas added
  2. customThe solution was then partitioned between EtOAc and 1N NaHCO3 aq. The organic layer
  3. washwas washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography
  8. customto give the indicated product

Sources & evidence

ORD record
ord-c89b665b907e4d389f7af17609d441c4
Source dataset
uspto-grants-2016_06
Patent number
US09365574B2

Reaction notes

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