4,4'-Dibromobenzil → HCID 59560832, compound

HRID 1176963Notes

Reaction equation

HRID 1176963 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]([C:12]2[CH:17]=[CH:16][C:15](Br)=[CH:14][CH:13]=2)=[O:11])=[O:9])=[CH:4][CH:3]=1.[CH2:19]([O:31][C:32]1[CH:37]=[CH:36][C:35]([CH:38]=[CH2:39])=[CH:34][C:33]=1[O:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30]>[Pd]>[CH2:19]([O:31][C:32]1[CH:37]=[CH:36][C:35]([CH:38]=[CH2:39])=[CH:34][C:33]=1[O:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].[CH2:41]([O:40][C:33]1[CH:34]=[C:35]([CH:38]=[CH:39][C:2]2[CH:7]=[CH:6][C:5]([C:8](=[O:9])[C:10]([C:12]3[CH:17]=[CH:16][C:15]([CH:39]=[CH:38][C:35]4[CH:36]=[CH:37][C:32]([O:31][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[C:33]([O:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52])[CH:34]=4)=[CH:14][CH:13]=3)=[O:11])=[CH:4][CH:3]=2)[CH:36]=[CH:37][C:32]=1[O:31][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52]

Participants

5

Reactant 2

HCID 964304,4'-DibromobenzilHCID 59560832HCID 59560832, compound

Product 2

HCID 59560832HCID 59560832, compoundYield 66%HCID 72326549HCID 72326549, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

1,2-Bis-dodecyloxy-4-vinyl-benzene (JYC-II-004-A) was synthesized in 66% yield according to a simplified Wittig reaction procedure reported by Gaset and co-workers.3 The Pd-catalyzed Heck coupling reaction between 4,4′-dibromobenzil and 1,2-bis-dodecyloxy-4-vinyl-benzene gave 1,2-bis-{4-[2-(3,4-bis-dodecyloxy-phenyl)-vinyl]-phenyl}-ethane-1,2-dione (JYC-II-007-A) in 76% yield as a bright yellow solid. Bis{1,2-di-{4-[2-(3,4-bis-dodecyloxy-phenyl)-vinyl]-phenyl}-ethane-1,2-dithiolene}nickel (JYC-II-014-A) was prepared from the reaction between JYC-II-007-A and excess phosphorus pentasulfide in 1,4-dioxane at 110° C. for 5 h, followed by the reaction with NiCl2.6H2O. The product was isolated as a dark green solid. The synthesis of JYC-II-014-A is shown in FIG. 2.

Workup

  1. customaccording to a simplified Wittig reaction procedure

Sources & evidence

ORD record
ord-99826f072d89473497891ad06cf2901d
Source dataset
uspto-grants-2010_11
Patent number
US07842830B2

Reaction notes

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