[(3-Chlorophenyl)methyl](triphenyl)phosphanium bromide → HCID 68941009, compound

HRID 1484146Notes

Reaction equation

HRID 1484146 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH2:13][CH2:14][C:15]1[CH:16]=[C:17]([CH:20]=[CH:21][CH:22]=1)[CH:18]=O.[Br-].[Cl:24][C:25]1[CH:26]=[C:27]([CH:48]=[CH:49][CH:50]=1)[CH2:28][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>>[Cl:24][C:25]1[CH:26]=[C:27]([CH:48]=[CH:49][CH:50]=1)/[CH:28]=[CH:18]/[C:17]1[CH:16]=[C:15]([CH2:14][CH2:13][CH2:12][N:3]2[C:2](=[O:1])[C:10]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[C:4]2=[O:11])[CH:22]=[CH:21][CH:20]=1.[Cl:24][C:25]1[CH:26]=[C:27]([CH:48]=[CH:49][CH:50]=1)/[CH:28]=[CH:18]\[C:17]1[CH:16]=[C:15]([CH2:14][CH2:13][CH2:12][N:3]2[C:2](=[O:1])[C:10]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[C:4]2=[O:11])[CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 16731599[(3-Chlorophenyl)methyl](triphenyl)phosphanium bromideHCID 577664653-(3-(1,3-Dioxoisoindolin-2-yl)propyl)benzaldehyde

Product 2

HCID 68941009HCID 68941009, compoundYield 30%HCID 68941730HCID 68941730, compoundYield 30%

Procedure

Phthalimide 29 was coupled with 3-chlorobenzyltriphenylphosphonium bromide. Purification by flash chromatography (5% EtOAc-hexanes) gave (E)-2-(3-(3-(3-chlorostyryl)phenyl)propyl)isoindoline-1,3-dione (0.100 g, 30%) and (Z)-2-(3-(3-(3-chlorostyryl)phenyl)propyl)isoindoline-1,3-dione (0.180 g, 30%) as colorless oils. Trans-isomer: 1H NMR (400 MHz, CDCl3) δ 7.80-7.84 (m, 2H), 7.68-7.72 (m, 2H), 7.50 (t, J=1.6 Hz, 1H), 7.37 (dt, J=7.6, 1.2 Hz, 1H), 7.35 (s, 1H), 7.29 (d, J=7.6 Hz, 1H), 7.21-7.26 (m, 3H), 7.12 (dt, J=6.4, 2.0 Hz, 1H), 7.03 (d, J=4.4 Hz, 2H), 3.78 (t, J=7.2 Hz, 2H), 2.72 (t, J=7.6 Hz, 2H), 2.05-2.12 (m, 2H).

Workup

  1. customPurification by flash chromatography (5% EtOAc-hexanes)

Sources & evidence

ORD record
ord-07301b3b4adf4c25906dff2573b09978
Source dataset
uspto-grants-2016_08
Patent number
US09421210B2

Reaction notes

Loading…