Cyclopropanecarbonitrile → 1-(4-Bromo-2-iodobenzyl)cyclopropanecarbonitrile

HRID 539295Notes

Reaction equation

HRID 539295 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][C:7]2([C:11]#[N:12])[CH2:10][CH2:9]C2)=[C:4]([I:15])[CH:3]=1.C1(C#N)CC1.BrC1C=CC(CBr)=C(I)C=1>>[Br:1][C:2]1[CH:14]=[CH:13][C:5]([CH2:6][C:7]2([C:11]#[N:12])[CH2:10][CH2:9]2)=[C:4]([I:15])[CH:3]=1

Participants

4

Reactant 3

HCID 79637CyclopropanecarbonitrileHCID 532313074-Bromo-1-(bromomethyl)-2-iodobenzeneHCID 679794311-(4-Bromo-2-iodobenzyl)cyclobutanecarbonitrile2×

Product 1

HCID 679793041-(4-Bromo-2-iodobenzyl)cyclopropanecarbonitrileYield 55%

Procedure

The title compound (2.1 g, 55% yield) was prepared as described for 1-(4-Bromo-2-iodobenzyl)cyclobutanecarbonitrile (Intermediate 37) starting from cyclopropanecarbonitrile (1.96 mL, 26.6 mmol) and 4-bromo-1-(bromomethyl)-2-iodobenzene (see Caruso, A.; Tovar, J., D. J. Org. Chem. 2011, 76, 2227-2239) (4.0 g, 10.6 mmol): 1H NMR (400 MHz, CDCl3) δ ppm 1.02-1.07 (m, 2 H), 1.33-1.37 (m, 2 H), 2.98 (s, 2 H), 7.35 (d, 1 H), 7.51 (dd, 1 H), 8.02 (d, 1H); MS (CI) m/z 362 [M+H]|.

Sources & evidence

ORD record
ord-5bfc9bb6c52244bd949f9e67b122095e
Source dataset
uspto-grants-2014_10
Patent number
US08865911B2

Reaction notes

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