Toluene → 2-(4-Bromophenyl)-6-phenylnaphthalene

HRID 1662917Notes

Reaction equation

HRID 1662917 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[CH:4][CH:3]=1.[C:9]1([C:15]2[CH:16]=[C:17]3[C:22](=[CH:23][CH:24]=2)[CH:21]=[C:20](B(O)O)[CH:19]=[CH:18]3)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O.C(COC)OC>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:20]2[CH:19]=[CH:18][C:17]3[C:22](=[CH:23][CH:24]=[C:15]([C:9]4[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=4)[CH:16]=3)[CH:21]=2)=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 115221-Bromo-4-iodobenzeneHCID 57539613(6-Phenylnaphthalen-2-yl)boronic acid

Product 1

HCID 575398112-(4-Bromophenyl)-6-phenylnaphthaleneYield 73.2%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
90 °C

Procedure

Under an argon gas atmosphere, 20.0 g (70.7 mmol) of 4-bromoiodobenzene, 17.5 g (70.7 mmol) of 6-phenylnaphthalene-2-boronic acid, 1.63 g (1.41 mmol) of tetrakis(triphenylphosphine) palladium(0), 200 mL of toluene, 50 mL of dimethoxyethane and 107 mL of 2M sodium carbonate solution were mixed, and stirred for 10 hours at 90 degrees C. Subsequently, the reaction mixture was cooled down to room temperature, added with water and stirred for one hour. After the solid precipitated during the reaction was separated by filtration, the obtained solid was cleansed with water, methanol, dimethoxyethane and toluene in this order. By dissolving the obtained solid in toluene and refining the solution by silica-gel column chromatography, 18.6 g of 2-(4-bromophenyl)-6-phenylnaphthalene was obtained at an yield of 73%.

Workup

  1. temperatureSubsequently, the reaction mixture was cooled down to room temperature
  2. stirringstirred for one hour
  3. customAfter the solid precipitated during the reaction
  4. customwas separated by filtration
  5. dissolutionBy dissolving the obtained solid in toluene

Sources & evidence

ORD record
ord-efe494dd18ed4cdbbef535cdf74e24c7
Source dataset
uspto-grants-2011_10
Patent number
US08034256B2

Reaction notes

Loading…