Chloroiodomethane → Methyl 3-(cyclopropyloxy)benzoate

HRID 1510137Notes

Reaction equation

HRID 1510137 reaction equation
[CH:1]([O:3][C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][CH:13]=1)[C:7]([O:9][CH3:10])=[O:8])=[CH2:2].I[CH2:15]Cl.C([Zn]CC)C>ClC(Cl)C>[CH:1]1([O:3][C:4]2[CH:5]=[C:6]([CH:11]=[CH:12][CH:13]=2)[C:7]([O:9][CH3:10])=[O:8])[CH2:15][CH2:2]1

Participants

5

Reactant 3

HCID 11644ChloroiodomethaneHCID 57336627Methyl 3-(ethenyloxy)benzoateHCID 178418750HCID 178418750, compound

Product 1

HCID 57336628Methyl 3-(cyclopropyloxy)benzoate

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of methyl 3-(vinyloxy)benzoate (0.83 g, 3.99 mmol) in dichloroethane (20 mL) was added iodochloromethane (1.09 mL, 14.9 mmol). The solution was cooled to 0° C. and diethyl zinc (1.0 M in hexanes, 7.48 mL, 7.48 mmol) was added. The cooling bath was removed and the reaction was stirred at rt for 30 min. The reaction mixture was quenched with 1N HCl, extracted with methylene chloride (three times), dried with MgSO4 and concentrate under vacuum to afford the desired product.

Workup

  1. customThe cooling bath was removed
  2. customThe reaction mixture was quenched with 1N HCl
  3. extractionextracted with methylene chloride (three times)
  4. dry with materialdried with MgSO4
  5. concentrationconcentrate under vacuum

Sources & evidence

ORD record
ord-9da18a6a5ae843529c2bb78ba53a0227
Source dataset
uspto-grants-2012_07
Patent number
US08211904B2

Reaction notes

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