2-chloro-N-methoxy-N,4-dimethylbenzamide → (2-Chloro-4-methylphenyl)(cyclopropyl)methanone

HRID 561450Notes

Reaction equation

HRID 561450 reaction equation
[CH:1]1([Mg]Br)[CH2:3][CH2:2]1.[Cl:6][C:7]1[CH:18]=[C:17]([CH3:19])[CH:16]=[CH:15][C:8]=1[C:9](N(OC)C)=[O:10]>C1COCC1.C(OCC)C>[Cl:6][C:7]1[CH:18]=[C:17]([CH3:19])[CH:16]=[CH:15][C:8]=1[C:9]([CH:1]1[CH2:3][CH2:2]1)=[O:10]

Participants

5

Reactant 2

HCID 583925172-chloro-N-methoxy-N,4-dimethylbenzamideHCID 178418630HCID 178418630, compound2×

Product 1

HCID 13175620(2-Chloro-4-methylphenyl)(cyclopropyl)methanone

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

7.7 ml (7.65 mmol) of a 1N cyclopropylmagnesium bromide solution in THF were added to 1.09 g (5.10 mmol) of the compound from Example 121A in 19 ml of diethyl ether, and the mixture was stirred at RT overnight. A further 7.7 ml (7.65 mmol) of a 1N cyclopropylmagnesium bromide solution in THF were added, and the mixture was stirred at RT overnight. The reaction mixture was added to ice-water and extracted with dichloromethane, the organic phase was dried over magnesium sulfate, filtered and concentrated, and the crude product was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient) to result in 326 mg (33% of theory) of the title compound.

Workup

  1. stirringthe mixture was stirred at RT overnight
  2. extractionextracted with dichloromethane
  3. dry with materialthe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthe crude product was purified by preparative HPLC (RP18 column; mobile phase: acetonitrile/water gradient)

Sources & evidence

ORD record
ord-8dce398ced9e44f59c5300807722c4b2
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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