Potassium Carbonate → (3-Bromophenyl)(3'-(dibenzo [b,d]furan-4-yl)-[1,1'-biphenyl]-3-yl)diphenylsilane

HRID 403147Notes

Reaction equation

HRID 403147 reaction equation
Br[C:2]1[CH:3]=[C:4]([Si:8]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([Br:27])[CH:22]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:5]=[CH:6][CH:7]=1.[CH2:28]1[C:36]23[CH:37]=[CH:38][CH:39]=[CH:40][C:35]2=CO[C:32]3=[C:31]([C:41]2[CH:42]=[C:43](B3OC(C)(C)C(C)(C)O3)[CH:44]=[CH:45][CH:46]=2)[CH:30]=[CH:29]1.[C:56]([O-:59])([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:27][C:23]1[CH:22]=[C:21]([Si:8]([C:4]2[CH:3]=[C:2]([C:45]3[CH:44]=[CH:43][CH:42]=[C:41]([C:31]4[C:32]5[O:59][C:56]6[CH:37]=[CH:38][CH:39]=[CH:40][C:35]=6[C:36]=5[CH:28]=[CH:29][CH:30]=4)[CH:46]=3)[CH:7]=[CH:6][CH:5]=2)([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:26]=[CH:25][CH:24]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 297508Bis(3-bromophenyl)diphenylsilaneHCID 710601992-(3-(Dibenzo[b,c]furan-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 86674050(3-Bromophenyl)(3'-(dibenzo [b,d]furan-4-yl)-[1,1'-biphenyl]-3-yl)diphenylsilaneYield 60.1%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture solution of bis(3-bromophenyl)diphenylsilane (8.01 g, 16.21 mmol), 2-(3-(dibenzo[b,c]furan-4-yl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (3.00 g, 8.10 mmol), K2CO3 (2.240 g, 16.21 mmol), Pd(PPh3)4 (0.15 g, 0.162 mmol) in toluene (200 mL) and water (50 mL) was refluxed under nitrogen overnight. After cooling to room temperature, the organic phase was isolated and evaporated to dryness. The residue was purified by column chromatography on silica gel with hexane:DCM (9/1 to 3/1, v/v) as eluent to yield (3-bromophenyl)(3′-(dibenzo [b,d]furan-4-yl)-[1,1′-biphenyl]-3-yl)diphenylsilane (3.2 g, 60%) as a white solid.

Workup

  1. customthe organic phase was isolated
  2. customevaporated to dryness
  3. customThe residue was purified by column chromatography on silica gel with hexane

Sources & evidence

ORD record
ord-d1db6c353a234c9f8281d8ec6c97ece1
Source dataset
uspto-grants-2014_06
Patent number
US08748012B2

Reaction notes

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