Phosphonium, [(2-methoxyphenyl)methyl]triphenyl-, bromide → (E)-2-(3-(3-(2-methoxystyryl)phenyl)propyl)isoindoline-1,3-dione

HRID 628617Notes

Reaction equation

HRID 628617 reaction equation
[Br-].[CH3:2][O:3][C:4]1[CH:29]=[CH:28][CH:27]=[CH:26][C:5]=1[CH2:6][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[O:30]=[C:31]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[C:33](=[O:40])[N:32]1[CH2:41][CH2:42][CH2:43][C:44]1[CH:45]=[C:46]([CH:49]=[CH:50][CH:51]=1)[CH:47]=O>>[CH3:2][O:3][C:4]1[CH:29]=[CH:28][CH:27]=[CH:26][C:5]=1/[CH:6]=[CH:47]/[C:46]1[CH:45]=[C:44]([CH2:43][CH2:42][CH2:41][N:32]2[C:33](=[O:40])[C:34]3[C:39](=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:31]2=[O:30])[CH:51]=[CH:50][CH:49]=1

Participants

3

Reactant 2

HCID 11294197Phosphonium, [(2-methoxyphenyl)methyl]triphenyl-, bromideHCID 577664653-(3-(1,3-Dioxoisoindolin-2-yl)propyl)benzaldehyde

Product 1

HCID 68943106(E)-2-(3-(3-(2-methoxystyryl)phenyl)propyl)isoindoline-1,3-dione

Procedure

2-Methoxybenzyltriphenylphosphonium bromide was coupled with phthalimide 29 to give (E)-2-(3-(3-(2-methoxystyryl)phenyl)propyl)isoindoline-1,3-dione as a white solid. Yield (0.5590 g, quant.), trans-/cis-isomer ratio 1:1. Trans-isomer: 1H NMR (400 MHz, DMSO-d6) δ 7.81-7.88 (m, 4H), 7.52-7.65 (m, 5H), 6.69-7.41 (m, 4H), 6.57 (d, J=16.8 Hz, 1H), 3.76 (s, 3H), 3.52 (t, J=6.8 Hz, 2H), 2.48 (t, J=8.0 Hz, 2H), 1.91-1.99 (m, 2H).

Sources & evidence

ORD record
ord-1404ab8f0cb0421fb59e5ab2e61289eb
Source dataset
uspto-grants-2016_04
Patent number
US09314467B2

Reaction notes

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