Diiodomethane → N-[4-Chloro-2-methoxy-5-(1-methylcyclopropyl)phenyl]acetamide

HRID 588869Notes

Reaction equation

HRID 588869 reaction equation
[Cl:1][C:2]1[C:7]([C:8]([CH3:10])=[CH2:9])=[CH:6][C:5]([NH:11][C:12](=[O:14])[CH3:13])=[C:4]([O:15][CH3:16])[CH:3]=1.[CH2:17](I)I.[Zn](CC)CC>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:7]([C:8]2([CH3:17])[CH2:10][CH2:9]2)=[CH:6][C:5]([NH:11][C:12](=[O:14])[CH3:13])=[C:4]([O:15][CH3:16])[CH:3]=1

Participants

5

Reactant 3

HCID 6346DiiodomethaneHCID 90455956N-[4-Chloro-2-methoxy-5-(1-methylethenyl)phenyl]acetamideHCID 178418750HCID 178418750, compound

Product 1

HCID 90455914N-[4-Chloro-2-methoxy-5-(1-methylcyclopropyl)phenyl]acetamideYield 77.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of N-(4-chloro-2-methoxy-5-(prop-1-en-2-yl)phenyl)acetamide (1.0 g, 4.17 mmol) in toluene (20 mL) at 0° C., CH2I2 (5.6 g, 20.86 mmol) and Et2Zn (41.7 mL, 41.7 mmol, 1.0 M in hexane) was added. The mixture was kept at 0° C. for 30 min, and then stirred at RT for 16 h. The reaction mixture was quenched with saturated NH4Cl solution and stirred for 15 min. The mixture was concentrated in vacuo to remove toluene and the resulting mixture was extracted with dichloromethane. The combined organic layer was washed with water and brine, dried over anhydrous Na2SO4, concentrated to afford the desired product (820 mg, 77% yield).

Workup

  1. customThe reaction mixture was quenched with saturated NH4Cl solution
  2. stirringstirred for 15 min
  3. concentrationThe mixture was concentrated in vacuo
  4. customto remove toluene
  5. extractionthe resulting mixture was extracted with dichloromethane
  6. washThe combined organic layer was washed with water and brine
  7. dry with materialdried over anhydrous Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-57134825d82a4f77a7bc2fc95323b3a2
Source dataset
uspto-grants-2016_01
Patent number
US09227978B2

Reaction notes

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