N-bromobutanimide → HCID 54536217, compound

HRID 566540Notes

Reaction equation

HRID 566540 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[CH:9][CH3:10].[Br:17]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>[Br:17][CH2:10][CH:9]=[C:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH3:1])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 544424051-(2-Methylphenyl)-1-phenyl-1-propene

Product 1

HCID 54536217HCID 54536217, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

TLC: rf=0.50 (SiO2; n-heptane/THF=7:3). 1-(2-Methylphenyl)-1-phenyl-1-propanol (10.4 g, 46 mmol) was dissolved into isopropanol (100 ml) and a 4 N sulphuric acid solution (50 ml) was added. The reaction mixture was heated at reflux temperature for 18 h and cooled to room temperature. Water (300 ml) was added and the mixture was extracted with dichloromethane (2×200 ml). The combined organic extracts was washed with a diluted sodium bicarbonate solution, dried (Na2SO4) and the solvent evaporated in vacuo to give 9.0 g (91%) of 1-(2-methylphenyl)-1-phenyl-1-propene. To a solution of 1-(2-methylphenyl)-1-phenyl-1-propene (9.0 g, 43 mmol) in carbon-tetrachloride (40 ml), N-bromosuccinimide (7.7 g, 43 mmol) and benzoylperoxide (0.1 g) were added. The reaction mixture was heated at reflux temperature for 18 h. The cooled reaction mixture was filtered through silica gel and the solvent evaporated in vacuo to give 9.3 g (76 %) of 3-bromo-1 (2-methylphenyl)-1-phenyl-1-propene.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux temperature for 18 h
  3. customThe cooled reaction mixture
  4. filtrationwas filtered through silica gel
  5. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-1005c33d85b84b2daf5b98d23c000f64
Source dataset
uspto-grants-2001_01
Patent number
US06174898B1

Reaction notes

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