[(3,5-Dimethylphenyl)methyl](triphenyl)phosphanium bromide → HCID 68944359, compound

HRID 242712Notes

Reaction equation

HRID 242712 reaction equation
[Br-].[CH3:2][C:3]1[CH:4]=[C:5]([CH:26]=[C:27]([CH3:29])[CH:28]=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>>[CH3:29][C:27]1[CH:26]=[C:5]([CH:4]=[C:3]([CH3:2])[CH:28]=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 10671681[(3,5-Dimethylphenyl)methyl](triphenyl)phosphanium bromideHCID 577664653-(3-(1,3-Dioxoisoindolin-2-yl)propyl)benzaldehyde

Product 1

HCID 68944359HCID 68944359, compound

Procedure

3,5-Dimethylbenzyltriphenylphosphonium bromide was coupled with phthalimide 29. Purification by flash chromatography (10 to 50% EtOAc-hexanes gradient) gave (E)-2-(3-(3-(3,5-dimethylstyryl)phenyl)propyl)isoindoline-1,3-dione as a white solid. Yield (0.3263 g, 55%): 1H NMR (400 MHz, DMSO-d6) δ 7.81-7.88 (m, 4H), 7.00-7.44 (m, 6H), 6.71-6.90 (m, 2H), 6.53 (s, 1H), 3.64 (t, J=7.2 Hz, 2H), 2.65 (t, J=7.2 Hz, 2H), 1.70-1.77 (m, 2H), 2.29 (s, 6H).

Workup

  1. customPurification by flash chromatography (10 to 50% EtOAc-hexanes gradient)

Sources & evidence

ORD record
ord-da4e294c1f0845b0881e738a09404912
Source dataset
uspto-grants-2014_02
Patent number
US08653142B2

Reaction notes

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