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

HRID 2104284Notes

Reaction equation

HRID 2104284 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-316372ca0ab04197baaf625b4257338c
Source dataset
uspto-grants-2009_08
Patent number
US07576239B2

Reaction notes

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