HCID 117833308, compound → HCID 117833114, compound

HRID 924537Notes

Reaction equation

HRID 924537 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:34]=[CH:33][C:14]([C:15]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][Br:32])=[CH:19][CH:18]=2)=O)=[CH:13][CH:12]=1>C1COCC1.Cl[Ti](Cl)(Cl)Cl.[Zn]>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:34]=[CH:33][C:14]([C:15]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][Br:32])=[CH:19][CH:18]=2)=[C:15]([C:14]2[CH:33]=[CH:34][C:11]([O:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][Br:1])=[CH:12][CH:13]=2)[C:17]2[CH:18]=[CH:19][C:20]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][Br:32])=[CH:21][CH:22]=2)=[CH:13][CH:12]=1

Participants

5

Reactant 1

HCID 117833308HCID 117833308, compound

Product 1

HCID 117833114HCID 117833114, compoundYield 62%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 24193Titanium TetrachlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In a suspension of 4,4′-bis(8-bromooctyloxy)benzophenone (1.0 g, 1.7 mmol) in 50 mL of THF were added TiCl4 (0.19 mL, 1.7 mmol) and Zn dust (0.22 g, 3.4 mmol). After refluxing for 20 h, the reaction mixture was cooled to room temperature and filtered. The solvent was evaporated under vacuum and the crude product was purified by a silica gel column using a chloroform/hexane (1:1 v/v) mixture as eluent. 1,1,2,2-tetrakis[4-(8-bromooctyloxy)phenyl]-ethene was obtained as yellow viscous liquid in 62% yield (0.6 g). Rf=0.5 (chloroform/hexane=1:1). 1H NMR (400 MHz, CDCl3), δ (ppm): 6.99-6.90 (m, 8H), 6.63-6.60 (m, 8H), 3.87-3.80 (m, 8H), 3.41-3.39 (m, 8H), 1.86-1.70 (m, 16H), 1.34-1.26 (m, 32H). 13C NMR (100 MHz, CDCl3), δ (ppm): 157.9, 137.5, 133.2, 129.9, 114.2, 68.3, 55.6, 34.7, 33.4, 29.9, 29.3, 28.7, 26.6.

Workup

  1. temperatureAfter refluxing for 20 h
  2. filtrationfiltered
  3. customThe solvent was evaporated under vacuum
  4. customthe crude product was purified by a silica gel column

Sources & evidence

ORD record
ord-4de631d6518d49ce823ed48e5704e7a3
Source dataset
uspto-grants-2016_03
Patent number
US09279806B2

Reaction notes

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