Reacción #1583833

ord-f001728f9054480c84a22788f799b943

Ecuación de reacción

O=C([O-])[O-].[K+].[K+]
potassium carbonate
CN(C)C=O
N,N-dimethylformamide
Clc1ccc(I)cc1CBr
2-(bromomethyl)-1-chloro-4-iodobenzene
Clc1ccc(I)cc1CBr
product
Clc1ccc(I)cc1CBr
2-(bromomethyl)-1-chloro-4-iodobenzene
CN(C)C=O
N,N-dimethylformamide
COC(=O)NCc1cc(I)ccc1Cl
title compound
COC(=O)NCc1cc(I)ccc1Cl
methyl[(2-chloro-5-iodo-phenyl)methyl]carbamate

Disolventes

Condiciones de reacción

Temperatura
110°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Temperaturacooled to room temperature
  2. 2
    OtroThe reaction mixture was partitioned between diethyl ether (200 mL) and water (200 mL)
  3. 3
    Otrothe organic layer was separated
  4. 4
    Lavadowashed with water (3×50 mL)
  5. 5
    Secadodried over magnesium sulfate
  6. 6
    Filtraciónfiltered
  7. 7
    Concentraciónconcentrated under reduced pressure

Procedimiento

To a mixture of potassium carbonate (4.30 g, 53.3 mmol) in N,N-dimethylformamide (47 mL) and methanol (5 mL) at 50° C. was added a solution of 2-(bromomethyl)-1-chloro-4-iodobenzene (i.e. the product of Step A) (5.20 g, 15.7 mmol) in N,N-dimethylformamide (10 mL). The reaction mixture was heated at 110° C. for 1 h and then cooled to room temperature. The reaction mixture was partitioned between diethyl ether (200 mL) and water (200 mL), the organic layer was separated, washed with water (3×50 mL), dried over magnesium sulfate, filtered and concentrated under reduced pressure to provide the title compound as a yellow oil (4.32 g).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US09198433B2uspto-grants-2015_12