Acetic Acid → 6-Bromo-1,2,3,4-tetrahydrocarbazole

HRID 403646Notes

Reaction equation

HRID 403646 reaction equation
Cl.[Br:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9]N)=[CH:5][CH:4]=1.[C:11](O)(=O)[CH3:12].C(=O)(O)[O-].[Na+]>C1(=O)CCCCC1>[Br:2][C:3]1[CH:8]=[C:7]2[C:6](=[CH:5][CH:4]=1)[NH:9][C:12]1[CH2:11][CH2:5][CH2:4][CH2:3][C:8]2=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 121574-Bromophenylhydrazine hydrochlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 2688776-Bromo-1,2,3,4-tetrahydrocarbazole

Reagents, catalysts & solvents 1

HCID 7967CyclohexanoneSolvent2×

Procedure

Cyclohexanone (1.16 mL, 11.2 mmol) and 4-bromo-phenylhydrazine hydrochloride (2.50 g, 11.2 mmol) were refluxed in cyclohexanone (18 mL) and acetic acid (AcOH) (12 L) for 24 h. The reaction mixture was treated with saturated sodium bicarbonate (Na2CO3) and extracted with ethyl acetate, dried (Na2CO3) and concentrated. The product was purified by column chromatography, giving 479 mg of compound 30 as a solid.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried (Na2CO3)
  3. concentrationconcentrated
  4. customThe product was purified by column chromatography

Sources & evidence

ORD record
ord-cc728d06680b4570a0af222d9319c9df
Source dataset
uspto-grants-2014_06
Patent number
US08748451B2

Reaction notes

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