3-(3-(1,3-Dioxoisoindolin-2-yl)propyl)benzaldehyde → (E)-2-(3-(3-(2,6-bis(trifluoromethyl)styryl)phenyl)propyl)isoindoline-1,3-dione

HRID 628625Notes

Reaction equation

HRID 628625 reaction equation
[Br-].[F:2][C:3]([F:35])([F:34])[C:4]1[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[C:5]=1[CH2:6][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[O:36]=[C:37]1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[C:39](=[O:46])[N:38]1[CH2:47][CH2:48][CH2:49][C:50]1[CH:51]=[C:52]([CH:55]=[CH:56][CH:57]=1)[CH:53]=O>>[F:35][C:3]([F:2])([F:34])[C:4]1[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:31])([F:32])[F:33])[C:5]=1/[CH:6]=[CH:53]/[C:52]1[CH:51]=[C:50]([CH2:49][CH2:48][CH2:47][N:38]2[C:39](=[O:46])[C:40]3[C:45](=[CH:44][CH:43]=[CH:42][CH:41]=3)[C:37]2=[O:36])[CH:57]=[CH:56][CH:55]=1

Participants

3

Reactant 2

HCID 577664653-(3-(1,3-Dioxoisoindolin-2-yl)propyl)benzaldehydeHCID 866321552,6-Bis(trifluoromethyl)benzyltriphenylphosphonium bromide

Product 1

HCID 86632157(E)-2-(3-(3-(2,6-bis(trifluoromethyl)styryl)phenyl)propyl)isoindoline-1,3-dione

Procedure

2,6-Bis(trifluoromethyl)benzyltriphenylphosphonium bromide was coupled with phthalimide 29 following the method used in Example 46. Purification by flash chromatography (30% diethyl ether-hexanes) gave (E)-2-(3-(3-(2,6-bis(trifluoromethyl)styryl)phenyl)propyl)isoindoline-1,3-dione as an oil. Yield (0.227 g, 62%): 1H NMR (400 MHz, DMSO-d6) δ 8.09 (d, J=8.0 Hz, 2H), 7.78-7.84 (m, 4H), 7.75 (t, J=7.6 Hz, 1H), 7.28-7.38 (m, 3H), 7.27 (t, J=7.6 Hz, 1H), 7.19 (d, J=7.2 Hz, 1H), 6.57 (d, J=16.8 Hz, 1H), 3.62 (t, J=6.8 Hz, 2H), 2.64 (t, J=8.0 Hz, 2H), 1.88-1.96 (m, 2H).

Workup

  1. customPurification by flash chromatography (30% diethyl ether-hexanes)

Sources & evidence

ORD record
ord-8839152b153646bea1810a62a2211872
Source dataset
uspto-grants-2016_04
Patent number
US09314467B2

Reaction notes

Loading…