Carbon Tetrachloride → HCID 57707841, compound

HRID 1397806Notes

Reaction equation

HRID 1397806 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9]([CH3:22])=[N:10][C:11]2[C:16]([N:17]=1)=[C:15]([C:18]([F:21])([F:20])[F:19])[CH:14]=[CH:13][CH:12]=2.[Br:23]N1C(C)(C)C(=O)N(Br)C1=O.C(Cl)(Cl)(Cl)Cl.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>>[Br:23][CH2:22][C:9]1[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])=[N:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][C:15]=2[C:18]([F:21])([F:19])[F:20])[N:10]=1

Participants

5

Reactant 4

HCID 5943Carbon TetrachlorideHCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 7187Benzoyl PeroxideHCID 57707825HCID 57707825, compound

Product 1

HCID 57707841HCID 57707841, compound

Procedure

3-(2-Chlorophenyl)-2-methyl-5-(trifluoromethyl)quinoxaline (0.9969 g, 3.089 mmol) and 1,3-dibromo-5,5-dimethylhydantoin (0.5299 g, 1.853 mmol) were suspended in carbon tetrachloride (30.89 mL, 3.089 mmol). To the mixture was added benzoyl peroxide (0.09977 g, 0.3089 mmol) and the mixture was heated at reflux. After 20 h, the mixture was cooled to room temperature and concentrated under reduced pressure. The residue was purified by silica gel column chromatography on a 80 g of Redi-Sep™ column using 0 to 5% gradient of EtOAc in hexane over 10 min, then 5% isocratic of EtOAc for 30 min, then 5 to 20% gradient of EtOAc in hexane over 20 min, then 20% isocratic of EtOAc for 4 min as eluent to give 2-(bromomethyl)-3-(2-chlorophenyl)-5-(trifluoromethyl)-quinoxaline as an off-white syrupy solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 8.48 (1 H, dd, J=8.6, 0.8 Hz), 8.37 (1 H, d, J=6.7 Hz), 8.09 (1 H, t, J=7.8 Hz), 7.55-7.77 (4 H, m), 4.73 (2 H, d, J=61.8 Hz); LC-MS (ESI) m/z 403.0 [M+11]+.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography on a 80 g of Redi-Sep™ column
  5. customover 10 min
  6. wait5% isocratic of EtOAc for 30 min
  7. wait5 to 20% gradient of EtOAc in hexane over 20 min

Sources & evidence

ORD record
ord-e2798e55b1a049b1880b7982664511a2
Source dataset
uspto-grants-2014_12
Patent number
US08901135B2

Reaction notes

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