2-(4-Bromophenyl)-N-methoxy-N-methylacetamide → 1-(4-Bromophenyl)butan-2-one

HRID 735682Notes

Reaction equation

HRID 735682 reaction equation
[CH2:1]([Mg]Cl)[CH3:2].[Br:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13](N(OC)C)=[O:14])=[CH:8][CH:7]=1>C1COCC1>[Br:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13](=[O:14])[CH2:1][CH3:2])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 189468992-(4-Bromophenyl)-N-methoxy-N-methylacetamideHCID 178461633HCID 178461633, compound

Product 1

HCID 154196931-(4-Bromophenyl)butan-2-oneYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a round bottom flask contained EtMgCl (10 mL, 2M in THF, 20 mmol) at 0° C., was added a solution of 70A (516 mg, 2 mmol) in 10 mL THF. The solution was stirred at rt for 30 min, then was quenched with sat. NH4Cl and extracted with EtOAc (3×20 mL). The organic layer washed with brine, dried (Na2SO4) and concentrated. Purification via flash chromatography (0-30% EtOAc/hexanes) afforded 70B (288 mg, 65%). MS (ESI) m/z 227.1 (M+H)+.

Workup

  1. customTo a round bottom flask contained
  2. customwas quenched with sat. NH4Cl
  3. extractionextracted with EtOAc (3×20 mL)
  4. washThe organic layer washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customPurification via flash chromatography (0-30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-684d985317904d0b8ae9ba32c7a12fa3
Source dataset
uspto-grants-2009_09
Patent number
US07592331B2

Reaction notes

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