2-(3,4-Dichlorophenyl)-N-methoxy-N-methylacetamide → 2-(3,4-Dichlorophenyl)-1-phenylethanone

HRID 924931Notes

Reaction equation

HRID 924931 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10](N(OC)C)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8].[C:16]1([Mg]Br)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[O:11])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

4

Reactant 2

HCID 152789332-(3,4-Dichlorophenyl)-N-methoxy-N-methylacetamideHCID 178418255HCID 178418255, compound

Product 1

HCID 27581442-(3,4-Dichlorophenyl)-1-phenylethanoneYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under N2, to a mixture of 2-(3,4-dichlorophenyl)-N-methoxy-N-methylacetamide (440 mg, 1.8 mmol) in anhydrous THF was added phenylmagnesium bromide (4.4 mL, 4.4 mmol) at −78° C., and the mixture was stirred for 3 hours. When TLC indicated that the starting material was consumed, the reaction mixture was diluted with EtOAc, washed with water and brine, concentrated, and purified by column chromatography (PE:EtOAc=20:1) to give Intermediate 6 (400 mg, yield 85%).

Workup

  1. customwas consumed
  2. additionthe reaction mixture was diluted with EtOAc
  3. washwashed with water and brine
  4. concentrationconcentrated
  5. custompurified by column chromatography (PE:EtOAc=20:1)

Sources & evidence

ORD record
ord-d682a83ed76147f9b9859cd653fcd87f
Source dataset
uspto-grants-2016_03
Patent number
US09283229B2

Reaction notes

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