m-Chloroperbenzoic acid → 8-Bromo-2-chloro-5h,11h-dibenzo[b,f]azocine-6-12-dione

HRID 2220199Notes

Reaction equation

HRID 2220199 reaction equation
[Br:1][C:2]1[CH:18]=[C:17]2[C:5]([CH2:6]C3C4C=C(Cl)C=CC=4[NH:9][C:8]=32)=[CH:4][CH:3]=1.[CH:19]1[CH:24]=[C:23]([Cl:25])[CH:22]=[C:21]([C:26]([O:28]O)=O)[CH:20]=1.C([O-])(O)=[O:31].[Na+]>C(Cl)(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[CH2:6][C:26](=[O:28])[C:21]3[CH:22]=[C:23]([Cl:25])[CH:24]=[CH:19][C:20]=3[NH:9][C:8](=[O:31])[C:17]=2[CH:18]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 597723853-Bromo-8-chloro-5,10-dihydro-indeno[1,2-b]indole

Product 1

HCID 597723788-Bromo-2-chloro-5h,11h-dibenzo[b,f]azocine-6-12-dioneYield 43%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution 3-Bromo-8-chloro-5,10-dihydro-indeno[1,2-b]indole (4.2 g, 13 mmol) in chloroform (150 mL) and 5% aqueous NaHCO3 (56 mL) was added mCPBA (7.5 g, 43 mmol) in chloroform (150 mL) dropwise over 30 minutes. The reaction mixture was stirred at room temperature for 2 hours and the layers were separated. The organic layer was washed with saturated aqueous NaHCO3, dried (Na2SO4), filtered and concentrated. The resulting oil was triturated with ether and filtered. The filter cake was washed with ether and dried in vacuo to give 8-Bromo-2-chloro-5H,11H-dibenzo[b,f]azocine-6-12-dione (2.0 g, 43%). 1HNMR (CDCl3) δ 7.67 (d, 1H, J+2.20 Hz), 7.59 (d, 1H, J=1.76 Hz), 7.42 (dd, 1H, J=7.92, 1.76 Hz), 7.32 (dd, 1H, J=8.01, 2.20 Hz), 7.02 (m, 2H), 4.44 (d, 1H, J=15.40 Hz), 3.85 (d, 1H, J=14.96 Hz). HPLC Rt=3.65 min.

Workup

  1. customthe layers were separated
  2. washThe organic layer was washed with saturated aqueous NaHCO3
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe resulting oil was triturated with ether
  7. filtrationfiltered
  8. washThe filter cake was washed with ether
  9. customdried in vacuo

Sources & evidence

ORD record
ord-d5dc71b4e490470fb70bcba424d510d5
Source dataset
uspto-grants-2008_08
Patent number
US07417040B2

Reaction notes

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