Sodium hydride → 9-(Benzenesulfonyl)-1-bromocarbazole

HRID 76375Notes

Reaction equation

HRID 76375 reaction equation
[Br:1][C:2]1[C:14]2[NH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:6]=2[CH:5]=[CH:4][CH:3]=1.[H-].[Na+].I[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[S:24](Cl)(=[O:26])=[O:25]>C1COCC1>[C:19]1([S:24]([N:13]2[C:14]3[C:2]([Br:1])=[CH:3][CH:4]=[CH:5][C:6]=3[C:7]3[C:12]2=[CH:11][CH:10]=[CH:9][CH:8]=3)(=[O:26])=[O:25])[CH:20]=[CH:21][CH:22]=[CH:23][CH:18]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 6274002-Iodobenzene-1-sulfonyl chlorideHCID 112303351-Bromo-9H-carbazole

Product 1

HCID 674051829-(Benzenesulfonyl)-1-bromocarbazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

19.6 g (80 mmol) of 1-bromocarbazole are initially introduced in 1000 ml of THF, and 8.9 g (223.3 mmol) of NaH (60% in oil) are added at 0° C. 24 g (80 mmol) of 2-iodobenzenesulfonyl chloride are subsequently added to the mixture, which is then stirred at 40° C. for 12 h. The organic phase is dried over MgSO4, and the solvent is removed in vacuo. The residue is recrystallised from acetone and finally sublimed in a high vacuum. Yield: 29 g (574 mmol), 72% of theory, purity according to HPLC 99.9%.

Workup

  1. dry with materialThe organic phase is dried over MgSO4
  2. customthe solvent is removed in vacuo
  3. customThe residue is recrystallised from acetone

Sources & evidence

ORD record
ord-3c43d7a676ae43afb3bbd4062c96f588
Source dataset
uspto-grants-2014_09
Patent number
US08835626B2

Reaction notes

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