Potassium Phosphate, Tribasic → (3-Bromophenyl)(3'-(dibenzo[b,d]thiophen-4-yl)-[1,1'-biphenyl]-3-yl)diphenylsilane

HRID 403145노트

반응식

HRID 403145 반응식
[CH:1]1[C:9]2[C:8]3[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=3[S:6][C:5]=2[C:4]([C:14]2[CH:15]=[C:16](B3OC(C)(C)C(C)(C)O3)[CH:17]=[CH:18][CH:19]=2)=[CH:3][CH:2]=1.Br[C:30]1[CH:31]=[C:32]([Si:36]([C:49]2[CH:54]=[CH:53][CH:52]=[C:51]([Br:55])[CH:50]=2)([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[CH:33]=[CH:34][CH:35]=1.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C(C)=CC=CC=1.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Br:55][C:51]1[CH:50]=[C:49]([Si:36]([C:32]2[CH:31]=[C:30]([C:16]3[CH:17]=[CH:18][CH:19]=[C:14]([C:4]4[C:5]5[S:6][C:7]6[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=6[C:9]=5[CH:1]=[CH:2][CH:3]=4)[CH:15]=3)[CH:35]=[CH:34][CH:33]=2)([C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=2)[C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:54]=[CH:53][CH:52]=1

참가 물질

8

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 297508Bis(3-bromophenyl)diphenylsilaneHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 595753552-(3-(Dibenzo[b,d]thiophen-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

생성물 1

HCID 86674048(3-Bromophenyl)(3'-(dibenzo[b,d]thiophen-4-yl)-[1,1'-biphenyl]-3-yl)diphenylsilane수율 30.6%

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 962Water용매HCID 7237O-Xylene용매

실험 절차

A mixture solution of 2-(3-(dibenzo[b,d]thiophen-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (6.0 g, 15.53 mmol), bis(3-bromophenyl)diphenylsilane (19.19 g, 38.8 mmol), Pd2(dba)3 (0.28 g, 0.31 mmol), SPhos (0.26 g, 0.62 mmol) and K3PO4 (3.30 g, 15.53 mmol) in xylene (150 mL) and water (15 mL) was refluxed under nitrogen at 120° C. overnight. After cooling to room temperature, the reaction mixture was quenched with water, extracted with DCM, washed with brine and water, and dried over Na2SO4. Upon evaporation of the solvent, the residue was purified by column chromatography on silica gel with hexane:DCM (9.5:0.5 to 9:1, v/v) as eluent. The crude product was dissolved in DCM, precipitated with methanol, and filtered to yield (3-bromophenyl)(3′-(dibenzo[b,d]thiophen-4-yl)-[1,1′-biphenyl]-3-yl)diphenylsilane (3.2 g, 30.6%) as a white powder.

후처리

  1. customthe reaction mixture was quenched with water
  2. extractionextracted with DCM
  3. washwashed with brine and water
  4. dry with materialdried over Na2SO4
  5. customUpon evaporation of the solvent
  6. customthe residue was purified by column chromatography on silica gel with hexane:DCM (9.5:0.5 to 9:1
  7. dissolutionThe crude product was dissolved in DCM
  8. customprecipitated with methanol
  9. filtrationfiltered

출처 및 근거

ORD 기록
ord-08dc7908259c401badcab96de10882c3
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748012B2

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