Benzaldehyde → HCID 5374623, compound

HRID 2356178Notes

Reaction equation

HRID 2356178 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.[Br-].BrC1C=CC(C[P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(=O)C1C=CC=CC=1.CC(C)([O-])C.[K+]>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5](/[CH:8]=[CH:9]/[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 6013891-Bromo-4-(2-phenylethenyl)benzeneHCID 2724858[(4-Bromophenyl)methyl]triphenylphosphanium bromideHCID 23665647Potassium tert-butoxide

Product 1

HCID 5374623HCID 5374623, compoundYield 29.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

First, a synthesis method of 4-bromostilbene is described. 25.3 g (49.5 mmol) of (4-bromobenzyl)triphenylphosphoniumbromide and 5.25 g (49.5 mmol) of benzaldehyde were put into a 500 mL three-necked flask and the air in the flask was replaced with nitrogen. 250 mL of tetrahydrofuran (THF) was added to the mixture. Then, a suspension in which 6.10 g (54.4 mmol) of potassium tert-butoxide was dissolved in 60 mL of THF was dropped to this mixture. After the dropping, the reaction mixture was stirred for 24 hours at room temperature. After the reaction, the reaction mixture was washed with water and the product was extracted with ethyl acetate from the water which was used for the washing. The obtained extraction solution and the organic layer, which was washed with water, were mixed and dried with magnesium sulfate. After the drying, the mixture was suction filtrated, and the filtrate was concentrated. The obtained residue was purified by silica gel column chromatography (developing solution: toluene). The obtained compound was washed with methanol and the solid was collected by suction filtration to give 3.75 g or a white powdered solid of (E)-4-bromostilbene (yield: 29.2%). A synthesis scheme (h-1) of 4-bromostilbene is shown below. Note that (Z)-4-bromostilbene was also observed in this reaction, but only (E)-4-bromostilbene was isolated and purified.

Workup

  1. additionwas dropped to this mixture
  2. customAfter the reaction
  3. washthe reaction mixture was washed with water
  4. extractionthe product was extracted with ethyl acetate from the water which
  5. extractionThe obtained extraction solution
  6. washthe organic layer, which was washed with water
  7. additionwere mixed
  8. dry with materialdried with magnesium sulfate
  9. filtrationfiltrated
  10. concentrationthe filtrate was concentrated
  11. customThe obtained residue was purified by silica gel column chromatography (developing solution: toluene)
  12. washThe obtained compound was washed with methanol
  13. filtrationthe solid was collected by suction filtration
  14. customto give 3.75 g

Sources & evidence

ORD record
ord-2854ca0791f04951934487216aada005
Source dataset
uspto-grants-2010_07
Patent number
US07758972B2

Reaction notes

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