Cyanocyclobutane → 1-(4-Bromo-2-iodobenzyl)cyclobutanecarbonitrile

HRID 1770895

Reaktionsgleichung

C([N-]C(C)C)(C)C.[Li+].[CH:9]1([C:13]#[N:14])[CH2:12][CH2:11][CH2:10]1.[Br:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22]Br)=[C:18]([I:24])[CH:17]=1>C1COCC1>[Br:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:9]2([C:13]#[N:14])[CH2:12][CH2:11][CH2:10]2)=[C:18]([I:24])[CH:17]=1

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

Lithium diisopropylamide (3.34 mL, 6.68 mmol), was added dropwise to a solution of cyclobutanecarbonitrile (0.417 g, 5.14 mmol) in THF (20 mL) at −78° C. under an argon atmosphere. The reaction mixture was stirred at −78° C. for 30 min, then was a solution of 4-bromo-1-(bromomethyl)-2-iodobenzene (see Caruso, A; Tovar, J., D. J. Org. Chem. 2011, 76, 2227-2239., 2.51 g, 6.68 mmol) in THF (8 mL) slowly added dropwise and the reaction was allowed to reach r.t. The mixture was stirred for another 3 h and then quenched with water. The reaction mixture was partitioned between water and EtOAc, the organic layer was dried over MgSO4 and concentrated to give a crude product which was purified by flash chromatography (eluent: heptane/ethylacetae 12:1) to afford the title compound (1.71 g, 89% yield): 1H NMR (500 MHz, CDCl3) δ ppm 2.08-2.34 (m, 4H), 2.47-2.58 (m, 2H), 3.18-3.23 (m, 2H), 7.29 (s, 1H), 7.49 (dd, 1H), 8.03 (d, 1H); GC MS (EI) m/z 375 M+.

Aufarbeitung

customto reach r.t
stirringThe mixture was stirred for another 3 h
customquenched with water
customThe reaction mixture was partitioned between water and EtOAc
dry with materialthe organic layer was dried over MgSO4
concentrationconcentrated
customto give a crude product which
customwas purified by flash chromatography (eluent: heptane/ethylacetae 12:1)

Quellen und Nachweise

ORD-Eintrag: ord-cde1484a4953463e8fa4e9d37da99e51
Quelldatensatz: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09248129B2

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