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

HRID 403145ノート

反応式

HRID 403145 の反応式
[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

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 962Water溶媒HCID 7237O-Xylene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-08dc7908259c401badcab96de10882c3
出典データセット
uspto-grants-2014_06
特許番号
US08748012B2

反応ノート

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