Reacción #595417

ord-5a24654fad78476b8a72c03057ef1813

Ecuación de reacción

Brc1ccc2[nH]c3ccc(Br)cc3c2c1
3,6-dibromocarbazole
[K+].[OH-]
KOH
CCOC(=O)CBr
Ethyl bromoacetate
CCOC(=O)Cn1c2ccc(Br)cc2c2cc(Br)ccc21
white solid
Rendimiento 96.4%
CCOC(=O)Cn1c2ccc(Br)cc2c2cc(Br)ccc21
ethyl 2-(3,6-dibromo-9H-carbazol-9-yl)acetate
Rendimiento 96.4%

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    workup.STIRRINGwas stirred at room temperature overnight
  2. 2
    OtroThe reaction crude
  3. 3
    Lavadowashed with 1M HCl and water
  4. 4
    SecadoThe organic layer was dried with MgSO4
  5. 5
    Concentraciónthe concentrated

Procedimiento

To a solution of 3,6-dibromocarbazole (325.0 mg, 1.0 mmol, 1 equiv) in anhydrous N,N-dimethylformamide (5 mL) was added crushed KOH (67.3 mg, 1.2 mmol, 1.2 equiv). The mixture was stirred for 30 minutes. Ethyl bromoacetate (277.2 μL, 2.5 mmol, 2.5 equiv) was added into the mixture and it was stirred at room temperature overnight. The reaction crude was diluted with ethyl acetate (30 mL) and washed with 1M HCl and water. The organic layer was dried with MgSO4 and the concentrated to afford 396.3 mg white solid as product (96.4%).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US09095572B2uspto-grants-2015_08