Allyl bromide → 4-[2-Propen-1-yl(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile

HRID 1173482Notes

Reaction equation

HRID 1173482 reaction equation
[F:1][C:2]([F:18])([F:17])[CH2:3][NH:4][C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[C:7]([C:13]([F:16])([F:15])[F:14])[CH:6]=1.[CH2:19](Br)[CH:20]=[CH2:21]>>[CH2:21]([N:4]([CH2:3][C:2]([F:17])([F:18])[F:1])[C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[C:7]([C:13]([F:16])([F:14])[F:15])[CH:6]=1)[CH:20]=[CH2:19]

Participants

3

Reactant 2

HCID 7841Allyl bromideHCID 431385374-((2,2,2-Trifluoroethyl)amino)-2-(trifluoromethyl)benzonitrile

Product 1

HCID 862395134-[2-Propen-1-yl(2,2,2-trifluoroethyl)amino]-2-(trifluoromethyl)benzonitrile

Procedure

Synthesized according to Example 61A using 4-(2,2,2-trifluoro-ethylamino)-2-trifluoromethyl-benzonitrile and allyl bromide: 1H NMR (300 MHz, CDCl3) δ 7.65 (d, J=8.8 Hz, 1H), 7.07 (d, J=2.4 Hz, 1H), 6.93 (dd, J=8.8, 2.6 Hz, 1H), 5.80 (ddt, J=17.2, 10.4, 5.0 Hz, 1H), 5.31 (app. d, J=10.6 Hz, 1H), 5.14 (app. d, J=17.2 Hz, 1H), 4.19-4.11 (m, 2H), 3.98 (q, J=8.6 Hz, 2H); MS (APCI) m/z 309 (M+1).

Workup

  1. customSynthesized

Sources & evidence

ORD record
ord-85ecad94736f4fe282559ac705518ee0
Source dataset
uspto-grants-2010_11
Patent number
US07834063B2

Reaction notes

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