Chloroiodomethane → Methyl 3-(cyclopropylmethyl)benzoate

HRID 1510122Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1510122
[CH2:1]([C:4]1[CH:5]=[C:6]([CH:11]=[CH:12][CH:13]=1)[C:7]([O:9][CH3:10])=[O:8])[CH:2]=[CH2:3].I[CH2:15]Cl.C([Zn]CC)C>ClC(Cl)C>[CH:2]1([CH2:1][C:4]2[CH:5]=[C:6]([CH:11]=[CH:12][CH:13]=2)[C:7]([O:9][CH3:10])=[O:8])[CH2:15][CH2:3]1

Komponenten

5

Edukt 3

HCID 11644ChloroiodomethaneHCID 10559182Methyl 3-allylbenzoateHCID 178418750HCID 178418750, Verbindung

Produkt 1

HCID 57336624Methyl 3-(cyclopropylmethyl)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 63651,1-DichloroethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of methyl 3-allylbenzoate (8.39 g, 47.6 mmol) in dichloroethane (100 mL) was added iodochloromethane (26.9 mL, 152 mmol). The solution was cooled to 0° C. and diethyl zinc (1.0 M in heptanes, 76.2 mL, 76.2 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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-064ca65b15a64e30a280984b8a9e73a6
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08211904B2

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