1,3-Dibromo-5,5-dimethylhydantoin → 2-(Bromomethyl)quinoxaline

HRID 1091082Notes

Reaction equation

HRID 1091082 reaction equation
[CH3:1][C:2]1[CH:11]=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[Br:30]N1C(C)(C)C(=O)N(Br)C1=O>C(Cl)(Cl)(Cl)Cl>[Br:30][CH2:1][C:2]1[CH:11]=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 7187Benzoyl PeroxideHCID 236862-Methylquinoxaline

Product 1

HCID 52877592-(Bromomethyl)quinoxaline

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a stirring solution of 2-methylquinoxaline (20.0 g, 155 mmol) and benzoyl peroxide (3 g, 12 mmol) in carbon tetrachloride (800 mL) was added 1,3-dibromo-5,5-dimethyl hydantoin (22 g, 77 mmol). The resulting mixture was irradiated with a spotlight (200 watt) for 1.5 hours. The mixture was cooled, filtered, and concentrated to afford crude product which was purified by HPLC (4:1 hexane/ethyl acetate) to yield 14.0 g (40%) of monobromomethyl product as a grey solid: 1H NMR (CDCl3): δ9.00 (s, 1H, ArH), 8.10 (m, 2H, ArH), 7.80 (m, 2H, ArH), 4.72 (s, 2H, BrCH2 --Ar); and 15.0 g (35%) of dibromomethyl product as a white solid: 1H NMR (CDCl3): δ9.39 (s, 1H, ArH), 8.15 (m, 2H, ArH), 7.90 (m, 2H, ArH), 6.76 (s, 1H, Br2CH--Ar).

Workup

  1. customThe resulting mixture was irradiated with a spotlight (200 watt) for 1.5 hours
  2. temperatureThe mixture was cooled
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto afford crude product which
  6. customwas purified by HPLC (4:1 hexane/ethyl acetate)
  7. customto yield 14.0 g (40%) of monobromomethyl product as a grey solid

Sources & evidence

ORD record
ord-82e5424c32084bd6808e076b625606e0
Source dataset
uspto-grants-1992_01
Patent number
US05084463

Reaction notes

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