Diiodomethane → 1-Phenyl-1-methylcyclopropane

HRID 1844703Notes

Reaction equation

HRID 1844703 reaction equation
[Zn](CC)[CH2:2]C.C(O)(C(F)(F)F)=O.C(I)I.[CH2:16]=[C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH3:18]>C(Cl)Cl>[CH3:16][C:17]1([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:2][CH2:18]1

Participants

6

Reactant 4

HCID 6346DiiodomethaneHCID 6422Trifluoroacetic acidHCID 7407Alpha-MethylstyreneHCID 178418750HCID 178418750, compound

Product 1

HCID 1375031-Phenyl-1-methylcyclopropane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent4×

Conditions

Temperature
0 °C

Procedure

To a solution of ZnEt2 (165 mL, 169 mmol) in DCM (160 mL) at 0° C. was added a solution of TFA (6.5 mL, 85 mmol) in DCM (80 mL) dropwise and the mixture was stirred at 0° C. for 30 min. Then to above mixture was added CH2I2 (6.6 mL, 85 mmol) in DCM (80 mL) dropwise and the mixture was stirred at 0° C. for 20 min, followed by adding dropwise a solution of prop-1-en-2-ylbenzene (5.0 g, 42.3 mmol) in DCM (80 mL). The mixture was stirred at rt for 30 min, quenched by brine (100 mL), extracted with DCM (2×100 mL) and the combined organic layers were dried over Na2SO4, filtered, concentrated and purified by CC (PE/EA=1/0 to 100/1) to afford compound P43a (3.4 g, 60%) as a yellow oil.

Workup

  1. stirringthe mixture was stirred at 0° C. for 20 min
  2. stirringThe mixture was stirred at rt for 30 min
  3. customquenched by brine (100 mL)
  4. extractionextracted with DCM (2×100 mL)
  5. dry with materialthe combined organic layers were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by CC (PE/EA=1/0 to 100/1)
  9. customto afford compound P43a (3.4 g, 60%) as a yellow oil

Sources & evidence

ORD record
ord-b7fb25a68d7244b2929e21380fb7cd5d
Source dataset
uspto-grants-2015_02
Patent number
US08946446B2

Reaction notes

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