Diiodomethane → 2-(3-Cyclopropylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HRID 891951

Reaktionsgleichung

Reaktionsgleichung von HRID 891951
[CH3:1][C:2]1([CH3:17])[C:6]([CH3:8])([CH3:7])[O:5][B:4]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]=[CH2:16])[CH:10]=2)[O:3]1.[CH2:18]([Zn]CC)C.ICI.[NH4+].[Cl-]>C1(C)C=CC=CC=1>[CH:15]1([C:11]2[CH:10]=[C:9]([B:4]3[O:3][C:2]([CH3:17])([CH3:1])[C:6]([CH3:7])([CH3:8])[O:5]3)[CH:14]=[CH:13][CH:12]=2)[CH2:18][CH2:16]1

Komponenten

6

Edukt 4

HCID 6346DiiodomethaneHCID 25517Ammonium ChlorideHCID 222401702-(3-Ethenylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 178418750HCID 178418750, Verbindung

Produkt 1

HCID 222402222-(3-Cyclopropylphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of 4,4,5,5-tetramethyl-2-(3-vinyl-phenyl)-[1,3,2]dioxaborolane (300 mg, 1.3 mmol) in toluene (10 ml) were added diethylzinc solution (1.1 N in toluene, 5.22 ml, 5.74 mmol) and diiodomethane (8.7 ml, 33 mmol). The reaction mixture was stirred for 1 hour at room temperature and then refluxed for 3 hours. The reaction mixture was poured on sat. NH4Cl solution (20 ml) and was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated in vacuo to provide 2-(3-cyclopropyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (69% yield), 1H-NMR (300 MHz, CDCl3): δ=7.12-7.82 (m, 4H), 1.35 (s, 12H), 1.28 (t, 1H), 0.90-0.96 (m, 2H), 0.72-0.78 (m, 2H).

Aufarbeitung

  1. temperaturerefluxed for 3 hours
  2. extractionwas extracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-16faa739c8524138aadf0fb8526258e3
Quelldatensatz
uspto-grants-2006_02
Patentnummer
US07005432B2

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