Benzoyl Peroxide → 4-(1-Bromo-3-oxoindan-2-ylidenemethyl)benzonitrile

HRID 59016Notes

Reaction equation

HRID 59016 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C:3]1=[CH:11][C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=1.[Br:20]N1C(=O)CCC1=O.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[Br:20][CH:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2](=[O:1])[C:3]1=[CH:11][C:12]1[CH:13]=[CH:14][C:15]([C:16]#[N:17])=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 3782734-(1-Oxoindan-2-ylidenemethyl)benzonitrile

Product 1

HCID 687526134-(1-Bromo-3-oxoindan-2-ylidenemethyl)benzonitrile

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

4-(1-Oxoindan-2-ylidenemethyl)benzonitrile (2.18 g, 8.9 mmol) was dissolved in carbon tetrachloride (40 mL). N-bromosuccinimide (1.58 g, 8.9 mmol) and benzoyl peroxide (100 mg) were added in one portion. Reaction mixture was reflux for 9 h, cooled down; precipitate was filtered off and washed with diethyl ether (10×30 mL) for removal of N-hydroxysuccinimide Precipitate was dried under vacuum, provided pure 15a.

Workup

  1. customReaction mixture
  2. temperaturewas reflux for 9 h
  3. temperaturecooled down
  4. filtrationprecipitate was filtered off
  5. washwashed with diethyl ether (10×30 mL) for removal of N-hydroxysuccinimide Precipitate
  6. customwas dried under vacuum

Sources & evidence

ORD record
ord-3950d79d0ef84a3386f9158353db47db
Source dataset
uspto-grants-2016_09
Patent number
US09439877B2

Reaction notes

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