N-bromobutanimide → HCID 14770215, compound

HRID 359213Notes

Reaction equation

HRID 359213 reaction equation
[CH3:1][C:2]1[C:3]2[C:15]([CH:16]=[CH:17][CH:18]=1)=[CH:14][C:6]1[C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=3[O:9][C:5]=1[CH:4]=2.[Br:19]N1C(=O)CCC1=O>C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>[Br:19][CH2:1][C:2]1[C:3]2[C:15]([CH:16]=[CH:17][CH:18]=1)=[CH:14][C:6]1[C:7]3[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=3[O:9][C:5]=1[CH:4]=2

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 14770214HCID 14770214, compound

Product 1

HCID 14770215HCID 14770215, compoundYield 101%

Reagents, catalysts & solvents 2

HCID 7187Benzoyl PeroxideCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To a RB flask was added 7-methyl-benzo[b]naphtho[2,3-d]furan (Cambridge Chemicals, Inc., 16.0 g, 0.07 mol), N-bromosuccinimide (Aldrich 12.8 g, 0.072 mol, recrystallized from H2 0 and dried under high vacuum overnight), a catalytic amount of benzoyl peroxide (0.01 g) and CCl4 (1 L). The mixture was refluxed for 2.5 h, cooled and filtered to remove the succinimide formed in the reaction. The solvent was then removed from the reaction mixture by rotary evaporation. The crude product was purified by flush chromatography on SiO2 using PhCH3 as the eluting solvent. The appropriate fractions were combined and the solvent once again removed by rotary evaporation to give 22.0 g of product. The material (which was one spot by TLC and pure by NMR) was used without further purification.

Workup

  1. temperatureThe mixture was refluxed for 2.5 h
  2. temperaturecooled
  3. filtrationfiltered
  4. customto remove the succinimide
  5. customformed in the reaction
  6. customThe solvent was then removed from the reaction mixture by rotary evaporation
  7. customThe crude product was purified
  8. customby flush chromatography on SiO2
  9. customthe solvent once again removed by rotary evaporation

Sources & evidence

ORD record
ord-838fa8ce21fa4c428534b1f4c11df56f
Source dataset
uspto-grants-1991_03
Patent number
US04999369

Reaction notes

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