Reacción #833518

ord-4648ec85394e4d479980e717bdadd2c8

Ecuación de reacción

CN(C)C=O
DMF
O=C1CCC(=O)N1Br
NBS
CCCCC(CC)COc1ccccc1OCC(CC)CCCC
1b
CCCCC(CC)COc1ccccc1OCC(CC)CCCC
1,2-di(2-ethylhexyloxy)benzene
O=C1CCC(=O)N1Br
NBS
CCCCC(CC)COc1ccc(Br)cc1OCC(CC)CCCC
4-bromo-1,2-di(2-ethylhexyloxy)benzene
Rendimiento 96.0%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    LavadoThe organic layer was washed with a saturated LiCl solution and water
  2. 2
    SecadoAfter drying with MgSO4 the solvent
  3. 3
    Otrowas removed under reduced pressure
  4. 4
    workup.DISTILLATIONThe remaining oil was distilled (160° C./0.01 mmHg)

Procedimiento

Solid NBS (26.21 g, 0.147 mol) was added to an ice cold CH2Cl2 solution (250 mL) of 1b under N2 in the absence of light. Just enough DMF was added (30 mL) to dissolve the NBS. The reaction mixture was allowed to warm to room temperature and then stirred for 12 h. The mixture was then poured into water. The organic layer was washed with a saturated LiCl solution and water. After drying with MgSO4 the solvent was removed under reduced pressure. The remaining oil was distilled (160° C./0.01 mmHg) to yield 4-bromo-1,2-di(2-ethylhexyloxy)benzene (2b) in 96% yield as a colorless oil.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07393503B2uspto-grants-2008_07