Toluene → HCID 18003130, compound

HRID 478916Notes

Reaction equation

HRID 478916 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[NH:12][CH:11]=[C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[O:9]2)=[CH:4][CH:3]=1.[C:19]1(C)C=CC=C[CH:20]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:19]([C:2]1[CH:7]=[CH:6][C:5]([N:8]2[NH:12][CH:11]=[C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[O:9]2)=[CH:4][CH:3]=1)=[CH2:20]

Participants

4

Reactant 2

HCID 1140Toluene2×HCID 18003126HCID 18003126, compound

Product 1

HCID 18003130HCID 18003130, compound

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

2-(4-Bromophenyl)-5-phenyl-oxadiazole (2.0 g, 6.64 mmol) was dissolved in degassed toluene (30 ml). Pd(PPh3)4 (0.15 g, 0.133 mmol) and nBu3Sn(CHCH2)(2.11 g, 6.64 mmol) were added under dry nitrogen. The solution was refluxed for 4 hours, cooled, and evaporated to give a yellow solid. This solid was dissolved in toluene (20 ml), silica added (20 g) and the solvent removed in vacuo. This solid was placed on top of a short column of silica and flushed with hexane to remove nBu3SnBr, and the column then stripped with methanol. The methanol was evaporated, and the residue recrystallised from hexane to give white crystals of 2-(4-vinylphenyl)-5-phenyloxadiazole, (m.pt. 83-84° C., lit.ii 82-84° C.)1.1 g, 67%. 1H NMR (CDCl3, 300 MHz) δ 8.1-8.0 (m, 4H, aromatic CH), 7.6-7.6 (m,5H, aromatic CH), 6.77 (d of d, 3JHH 17.4 Hz and 10.8 Hz, ChCH2), 6.90 (d, 3JHH 17.4 Hz, CHCH2), (d of d, 3JHH 10.8 Hz, CHCH2).

Workup

  1. temperatureThe solution was refluxed for 4 hours
  2. temperaturecooled
  3. customevaporated
  4. customto give a yellow solid
  5. additionsilica added (20 g)
  6. customthe solvent removed in vacuo
  7. customflushed with hexane
  8. customto remove nBu3SnBr
  9. customThe methanol was evaporated
  10. customthe residue recrystallised from hexane

Sources & evidence

ORD record
ord-4ba190ebbbf64fa899de5373f9fd846b
Source dataset
uspto-grants-2003_11
Patent number
US06642332B1

Reaction notes

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