1,5-Dibromopentane → 1-[3-(Trifluoromethyl)phenyl]cyclohexane-1-carbonitrile

HRID 333264

Reaction equation

[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[C:5]([CH2:9][C:10]#[N:11])[CH:6]=[CH:7][CH:8]=1.Br[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]Br>>[F:1][C:2]([F:12])([F:13])[C:3]1[CH:4]=[C:5]([C:9]2([C:10]#[N:11])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH:6]=[CH:7][CH:8]=1

Participants

Reactant 2

HCID 81001,5-Dibromopentane

HCID 75360m-Trifluoromethylphenylacetonitrile

Product 1

HCID 289376841-[3-(Trifluoromethyl)phenyl]cyclohexane-1-carbonitrileYield 96%

Procedure

The title compound was prepared from 2-(3-(trifluoromethyl)phenyl)acetonitrile (3.463 ml, 22.2 mmol) and 1,5-dibromopentane (3.324 ml, 24.4 mmol) according to General Procedure J to yield 1-(3-(trifluoromethyl)phenyl)cyclohexane-carbonitrile (5.40 g, 90%) as a clear oil. 1H NMR (CDCl3) δ 1.26-1.39 (m, 1H), 1.76-1.88 (m, 7H), 2.17 (d, J=11.2 Hz, 2H), 7.51-7.60 (m, 3H), 7.73 (s, 1H). 13C NMR (CDCl3) δ 23.7, 25.0, 37.5, 44.6, 122.5, 125.0, 125.1, 126.0, 129.5, 130.0, 142.8,GC-MS m/z 253.

Sources & evidence

ORD record: ord-3676b69b7c4d406d84722d393006e827
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08877975B2

Linked notes

Loading…