Potassium Carbonate → (5-Bromo-3'-(dibenzo[b,d]furan-4-yl)[1,1'-biphenyl]-3-yl)triphenylsilane

HRID 713590ノート

反応式

HRID 713590 の反応式
Br[C:2]1[CH:3]=[C:4]([Si:9]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[C:6]([Br:8])[CH:7]=1.C1[C:36]2[C:35]3[CH:37]=[CH:38][CH:39]=[CH:40][C:34]=3[O:33][C:32]=2[C:31](C2C=C(B3OC(C)(C)C(C)(C)O3)C=CC=2)=CC=1.C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:8][C:6]1[CH:5]=[C:4]([Si:9]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:3]=[C:2]([C:7]2[CH:2]=[CH:3][CH:4]=[C:36]([C:35]3[C:34]4[O:33][C:32]5[CH:12]=[CH:11][CH:10]=[CH:15][C:31]=5[C:40]=4[CH:39]=[CH:38][CH:37]=3)[CH:6]=2)[CH:7]=1

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 575885922-(3-(Dibenzo[b,d]furan-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 58926930HCID 58926930、化合物

生成物 1

HCID 86700951(5-Bromo-3'-(dibenzo[b,d]furan-4-yl)[1,1'-biphenyl]-3-yl)triphenylsilane収率 45.8%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 1140Toluene溶媒

実験手順

A solution of (3,5-Dibromophenyl)triphenylsilane (4.27 g, 8.64 mmol), 2-(3-(dibenzo[b,d]furan-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.6 g, 4.32 mmol), Pd(PPh3)4 (0.100 g, 0.086 mmol) and K2CO3 (1.792 g, 12.96 mmol) in toluene (100 mL) and water (10 mL) was refluxed under nitrogen overnight. After cooling to room temperature, the organic phase was isolated, and the solvent was evaporated. The residue was purified by column chromatography on silica gel with hexane/DCM (4/1 to 3/1, v/v) as eluent to yield (5-Bromo-3′-(dibenzo[b,d]furan-4-yl)[1,1′-biphenyl]-3-yl)triphenylsilane (1.3 g, 45%) as a white solid.

後処理

  1. customthe organic phase was isolated
  2. customthe solvent was evaporated
  3. customThe residue was purified by column chromatography on silica gel with hexane/DCM (4/1 to 3/1

出典と根拠

ORDレコード
ord-55d9814bab71498bac825b61adfd2d20
出典データセット
uspto-grants-2015_11
特許番号
US09184399B2

反応ノート

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