4-Bromobenzophenone → HCID 66591017, compound

HRID 589261Notes

Reaction equation

HRID 589261 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=O)=[CH:4][CH:3]=1>C1COCC1.Cl[Ti](Cl)(Cl)Cl.[Zn]>[Br:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:6]([C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:15][CH:14]=2)[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 70304-Bromobenzophenone

Product 1

HCID 66591017HCID 66591017, compoundYield 95%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 24193Titanium TetrachlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

In a suspension of 4-bromobenzophenone (5 g, 19.2 mmol) in 50 mL of THF were added TiCl4 (2.14 mL, 19.2 mmol) and Zn dust (2.48 g, 38.4 mmol). After reflux 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 hexane as eluent. 1,2-Bis(4-bromophenyl)-1,2-diphenylethene (5) was obtained as white solid in 95% yield (4.3 g). 1H NMR (CDCl3, 300 MHz), δ (ppm): 7.27 7.19 (m, 4H), 7.15 7.09 (m, 6H), 6.98 (m, 4H), 6.90 6.86 (m, 4H). 13C NMR (CDCl3, 75 MHz), δ (TMS, ppm): 133.0, 131.3, 131.2, 131.0, 128.1, 127.9, 127.8, 127.0, 126.9. MS (TOF): m/e 489.9 (M+, calcd. 490.0).

Workup

  1. temperatureAfter reflux 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-2b3a801411d34b68a4169ba611a3148d
Source dataset
uspto-grants-2016_01
Patent number
US09228949B2

Reaction notes

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