Carbon tetrabromide → N-(2-bromoethyl)-6-methoxycarbazole-3,4-dicarboximide

HRID 374030Notes

Reaction equation

HRID 374030 reaction equation
O[CH2:2][CH2:3][N:4]1[C:20](=[O:21])[C:19]2[C:18]3[C:17]4[C:12](=[CH:13][CH:14]=[C:15]([O:22][CH3:23])[CH:16]=4)[NH:11][C:10]=3[CH:9]=[CH:8][C:7]=2[C:5]1=[O:6].C(Br)(Br)(Br)[Br:25].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CN(C)C=O>[Br:25][CH2:2][CH2:3][N:4]1[C:20](=[O:21])[C:19]2[C:18]3[C:17]4[C:12](=[CH:13][CH:14]=[C:15]([O:22][CH3:23])[CH:16]=4)[NH:11][C:10]=3[CH:9]=[CH:8][C:7]=2[C:5]1=[O:6]

Participants

5

Reactant 3

HCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 19808818HCID 19808818, compound

Product 1

HCID 19808805N-(2-bromoethyl)-6-methoxycarbazole-3,4-dicarboximideYield 42.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 4.5 ml of N,N-dimethylformamide was dissolved 450 mg of N-(2-hydroxyethyl)-6-methoxycarbazole-3,4-dicarboximide. Thereto were added 1.06 g of carbon tetrabromide and 840 mg of triphenylphosphine. The mixture was stirred at room temperature for 2 hours. The solvent was removed by distillation under reduced pressure. The residue was mixed with 50 ml of water and 50 ml of ethyl acetate. The mixture was stirred at room temperature for 10 minutes. The resulting insoluble material was removed by filtration. The organic layer was separated from the filtrate, washed with an aqueous saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was recrystallized from n-propanol to obtain 230 mg (yield: 42%) of N-(2-bromoethyl)-6-methoxycarbazole-3,4-dicarboximide as yellow crystals.

Workup

  1. customThe solvent was removed by distillation under reduced pressure
  2. additionThe residue was mixed with 50 ml of water and 50 ml of ethyl acetate
  3. stirringThe mixture was stirred at room temperature for 10 minutes
  4. customThe resulting insoluble material was removed by filtration
  5. customThe organic layer was separated from the filtrate
  6. washwashed with an aqueous saturated sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was removed by distillation under reduced pressure
  9. customThe residue was recrystallized from n-propanol

Sources & evidence

ORD record
ord-eae2276fc8804700acc5990d8b64f2a0
Source dataset
uspto-grants-1992_11
Patent number
US05166204

Reaction notes

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