Sodium Carbonate → 4-(4-Bromophenyl)dibenzo[b,d]furan

HRID 1893109Notes

Reaction equation

HRID 1893109 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].I[C:8]1[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][CH:9]=1.[CH:15]1[C:23]2[C:22]3[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=3[O:20][C:19]=2[C:18](B(O)O)=[CH:17][CH:16]=1>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.C1(C)C=CC=CC=1>[Br:14][C:11]1[CH:12]=[CH:13][C:8]([C:27]2[C:21]3[O:20][C:19]4[CH:18]=[CH:17][CH:16]=[CH:15][C:23]=4[C:22]=3[CH:24]=[CH:25][CH:26]=2)=[CH:9][CH:10]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 115221-Bromo-4-iodobenzeneHCID 2734328Dibenzofuran-4-boronic acid

Product 1

HCID 590220984-(4-Bromophenyl)dibenzo[b,d]furan

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

Under an argon atmosphere, 300 mL of toluene and 150 mL of a 2-M aqueous solution of sodium carbonate were added to 28.3 g (100 mmol) of 4-iodobromobenzene, 22.3 g (105 mmol) of dibenzofuran-4-boronic acid, and 2.31 g (2.00 mmol) of tetrakis(triphenylphosphine)palladium(0), and the mixture was refluxed under heat for 10 hours.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heat for 10 hours

Sources & evidence

ORD record
ord-3c109843142042b5aaa7b505030e773d
Source dataset
uspto-grants-2013_08
Patent number
US08512875B2

Reaction notes

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