Reacción #1458418

ord-e46395004e664909bfd2812dc56a087b

Ecuación de reacción

COB(OC)c1c(C(C)C)cc(C(C)C)cc1C(C)C
(2,4,6-triisopropylphenyl)dimethoxyborane
[Br-].[Br-].[Mg+2]
magnesium bromide
CCCCCCCCOc1cc(-c2cc(OCCCCCCCC)c(Br)cc2I)c(I)cc1Br
4,4′-dibromo-2,2′-diiodo-5,5′-dioctyloxy-1,1′-biphenyl
CCCCCC
hexane
CCCCCCCCOc1cc2c(cc1Br)B(c1c(C(C)C)cc(C(C)C)cc1C(C)C)c1cc(Br)c(OCCCCCCCC)cc1-2
3,7-dibromo-5-(2,4,6-triisopropylphenyl)-2,8-dioctyloxy-5H-dibenzo(b, d)borole

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    workup.ADDITIONwas added
  2. 2
    workup.DISSOLUTIONto dissolve the same
  3. 3
    workup.STIRRINGstirred for 1 hour
  4. 4
    TemperaturaThe mixture was cooled again to −90° C.
  5. 5
    TemperaturaAfter warming
  6. 6
    Otroto react
  7. 7
    Temperaturaunder reflux for 12 hours

Procedimiento

2.0 g of 4,4′-dibromo-2,2′-diiodo-5,5′-dioctyloxy-1,1′-biphenyl synthesized as above was put in a 100 ml flask in an atmosphere of nitrogen and 20 ml of tetrahydrofuran was added to dissolve the same. Then, the tetrahydrofuran solution was cooled to −90° C. and 3.4 ml of 1.6M hexane solution was added dropwise. After 1-hour stirring, a solution of 1.5 g of magnesium bromide in 20 ml of tetrahydrofuran was added, warmed to room temperature, and stirred for 1 hour. The mixture was cooled again to −90° C., and 1.01 g of (2,4,6-triisopropylphenyl)dimethoxyborane was added. After warming, the mixture was allowed to react under reflux for 12 hours.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07157154B2uspto-grants-2007_01