Diiodomethane → 5'-Bromo-2',3'-dihydrospiro[cyclopropane-1,1'-indene]

HRID 855312Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 855312
[CH2:1]([Zn]CC)C.FC(F)(F)C(O)=O.C(I)I.[Br:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[C:22](=[CH2:26])[CH2:21][CH2:20]2>>[Br:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[C:22]1([CH2:1][CH2:26]1)[CH2:21][CH2:20]2

Komponenten

5

Edukt 4

HCID 6346DiiodomethaneHCID 6422Trifluoroacetic acidHCID 588409305-bromo-1-methylene-2,3-dihydro-1H-indeneHCID 178418750HCID 178418750, Verbindung

Produkt 1

HCID 695138995'-Bromo-2',3'-dihydrospiro[cyclopropane-1,1'-indene]Ausbeute 95 %

Versuchsvorschrift

The title compound was synthesized in analogy to example S87 using diethyl zinc (3.25 ml, 1M solution in hexane, 3.25 mmol), trifluoroacetic acid (251 μl, 3.25 mmol), CH2I2 (262 μl, 3.25 mmol) and 5-bromo-1-methyleneindan (340 mg, 1.63 mmol). The isolated residue was purified by flash column chromatography (100% pentane) to give 5′-bromo-2′,3′dihydro-spiro[cyclopropane1,1′-[1H]indene](345 mg, 95%) as a colorless oil. 1H NMR (CDCl3, 300 MHz): δ 7.40-7.29 (m, 3H), 3.02 (apt t, J=7.5 Hz, 2H), 2.11 (apt t, J=7.5 Hz, 2H), 0.96-0.84 (m, 4H).

Aufarbeitung

  1. customThe isolated residue was purified by flash column chromatography (100% pentane)

Quellen und Nachweise

ORD-Eintrag
ord-9ddf1306b93441acb3699c69273971fa
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07259183B2

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