Benzoyl Peroxide → HCID 69425360, compound

HRID 1181854Notes

Reaction equation

HRID 1181854 reaction equation
[CH3:1][C:2]1[C:7]([C:8]2[CH:17]=[CH:16][C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=2)=[CH:6][CH:5]=[CH:4][C:3]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C1C(=O)[N:46](Br)[C:44](=O)C1.[C-]#N.[Na+]>C(Cl)Cl.CN(C=O)C.C(OCC)(=O)C>[CH:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:16]=[CH:17][C:8]=1[C:7]1[C:2]([CH2:1][C:44]#[N:46])=[C:3]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:4]=[CH:5][CH:6]=1

Participants

8

Reactant 4

HCID 7187Benzoyl PeroxideHCID 8929Sodium CyanideHCID 67184N-bromobutanimideHCID 86607237HCID 86607237, compound

Product 1

HCID 69425360HCID 69425360, compoundYield 52.9%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-(2-methyl-1,1′-biphenyl-3-yl)naphthalene (2.0 g, 6.8 mmol) and 200 mg of benzoyl peroxide was refluxed, then NBS (1.21 g, 6.8 mmol) was added. The reaction mixture was refluxed overnight, diluted with methylene chloride, washed with water and dried over MgSO4. Removal of solvent under reduced pressure gave a crude product. The crude product was dissolved in 20 mL of DMF and sodium cyanide (0.65 g, 13 mmol) was added. The reaction was stirred at room temperature for 2 hours, diluted with ethyl acetate, washed with water and dried over MgSO4. Removal of solvent under reduced pressure gave a crude product that was purified by silica gel chromatography eluting with 0.4% ethyl acetate/hexanes to give 1.15 g of (3-naphthalen-2-yl-biphenyl-2-yl)-acetonitrile: 1H NMR (CDCl3): δ 3.43 (s, 2H), 7.30-7.60 (m, 11H), 7.80-7.95 (m, 4H).

Workup

  1. temperatureThe reaction mixture was refluxed overnight
  2. washwashed with water
  3. dry with materialdried over MgSO4
  4. customRemoval of solvent under reduced pressure
  5. customgave a crude product
  6. washwashed with water
  7. dry with materialdried over MgSO4
  8. customRemoval of solvent under reduced pressure
  9. customgave a crude product that
  10. customwas purified by silica gel chromatography
  11. washeluting with 0.4% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-b3be270877eb4c10913583ec5dae3933
Source dataset
uspto-grants-2007_10
Patent number
US07285682B2

Reaction notes

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