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

HRID 363000Notes

Reaction equation

HRID 363000 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:5]=2[CH:6]=1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.[Br:32]N1C(C)(C)C(=O)N(Br)C1=O>C(Cl)(Cl)(Cl)Cl>[Br:32][CH2:1][C:2]1[O:3][C:4]2[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:5]=2[CH:6]=1

Participants

5

Reactant 3

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 7187Benzoyl PeroxideHCID 44874532-Methyl-5-nitrobenzofuran

Product 1

HCID 114141792-(Bromomethyl)-5-nitro-1-benzofuranYield 121.1%

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a stirring solution of the above benzofuran (5.00 g, 28.25 mmol) and benzoyl peroxide (0.68 g, 2.83 mmol) in carbon tetrachloride (200 mL) was added 1,3-dibromo-5,5-dimethylhydantoin (4.04 g, 14.12 mmol). The mixture was irradiated with a 200 watt lamp while stirring for 1 hour, cooled and partitioned between dichloromethane/water. The organic phase was washed with water (2×100 mL) and brine (2×100 mL), dried (MgSO4), decolorized (charcoal), and concentrated in vacuo to afford 7.12 g of crude product. Recrystallization from ethyl acetate/hexane afforded 4.38 g (61%) of 2-bromomethyl-5-nitro-benzofuran as an off-white solid: 1H NMR (CDCl3): δ 8.49 (d, 1H), 8.25 (dd, 1H), 7.58 (d, 1H), 6.91 (s, 1H), 4.59 (s, 2H).

Workup

  1. customThe mixture was irradiated with a 200 watt lamp
  2. temperaturecooled
  3. custompartitioned between dichloromethane/water
  4. washThe organic phase was washed with water (2×100 mL) and brine (2×100 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customto afford 7.12 g of crude product
  8. customRecrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-107b6234aa994c4a858116bb3bf3fce3
Source dataset
uspto-grants-1999_02
Patent number
US05872139

Reaction notes

Loading…