Sodium Carbonate → 1-(4-bromophenyl)naphthalene

HRID 1660660Notes

Reaction equation

HRID 1660660 reaction equation
[C:1]1(B(O)O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Br:14][C:15]1[CH:20]=[CH:19][C:18](I)=[CH:17][CH:16]=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.C1(C)C=CC=CC=1>[Br:14][C:15]1[CH:20]=[CH:19][C:18]([C:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=2)=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 115221-Bromo-4-iodobenzeneHCID 2545321-Naphthaleneboronic acid

Product 1

HCID 112083381-(4-bromophenyl)naphthaleneYield 81%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

Under an argon gas atmosphere, 200.0 g (1.163 mol) of 1-naphthaleneboronic acid, 329.0 g (1.163 mol) of 4-bromoiodobenzene, 26.9 g (23.3 mmol) of tetrakis(triphenylphosphine) palladium(0), 3.7 L of toluene and 1.74 L of 2M sodium carbonate solution were mixed, and stirred for 24 hours at 90 degrees C. After the reaction in the mixture was over, the mixture experienced filtration, through which aqueous phase thereof was eliminated. After organic phase thereof was cleansed by water and dried with magnesium sulfate, toluene was distilled away under reduced pressure. Residue thereof was refined by silica-gel column chromatography, such that 268 g of 1-(4-bromophenyl)naphthalene was obtained with an yield of 81%.

Workup

  1. customAfter the reaction in the mixture
  2. filtrationfiltration
  3. dry with materialdried with magnesium sulfate, toluene
  4. distillationwas distilled away under reduced pressure
  5. customwas obtained with an yield of 81%

Sources & evidence

ORD record
ord-d88240d1a2d548bc90f332767cbaf84d
Source dataset
uspto-grants-2011_10
Patent number
US08029697B2

Reaction notes

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