N-Methoxy-N-methylacetamide → 1-(3-Bromophenyl)propan-2-one

HRID 1446386Notes

Reaction equation

HRID 1446386 reaction equation
CON(C)[C:4](=[O:6])[CH3:5].[Br:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[CH2:12][Mg]Br>CCOCC>[Br:8][C:9]1[CH:10]=[C:11]([CH2:12][C:4]([CH3:5])=[O:6])[CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 537505N-Methoxy-N-methylacetamideHCID 178419662HCID 178419662, compound

Product 1

HCID 27340931-(3-Bromophenyl)propan-2-one

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of N-methoxy-N-methylacetamide (10 g, 0.10 mol) in 200 mL of ether at 0° C. was added 3-bromobenzylmagnesium bromide (0.25 M, 200 mL, 50 mmol). After stirring at 0° C. for 2 h, the reaction mixture was partitioned between hexane and saturated aqueous ammonium chloride. The organic layer was separated, washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated to dryness to give the title compound, which was used without further purification. 1H NMR (500 MHz, CD3OD): δ 7.5-7.1 (m, 4H), 3.78 (s, 2H), 2.19 (s, 3H).

Workup

  1. customthe reaction mixture was partitioned between hexane and saturated aqueous ammonium chloride
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-3db2f34bde4a4bbba577c7b81c7737aa
Source dataset
uspto-grants-2010_02
Patent number
US07667053B2

Reaction notes

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