Sodium Carbonate → 2-(4-Bromophenyl)naphthalene

HRID 1045294Notes

Reaction equation

HRID 1045294 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1B(O)O.[Br:14][C:15]1[CH:20]=[CH:19][C:18](I)=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Na+].[Na+]>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:15]1[CH:20]=[CH:19][C:18]([C:2]2[CH:3]=[CH:4][C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[CH:1]=2)=[CH:17][CH:16]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 115221-Bromo-4-iodobenzeneHCID 2734375(Naphthalen-2-yl)boronic acid

Product 1

HCID 54617522-(4-Bromophenyl)naphthaleneYield 67%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent2×

Conditions

Temperature
90 °C

Procedure

Under an argon gas atmosphere, 70.0 g (407 mmol) of 2-naphthaleneboronic acid, 115.10 g (407 mmol) of 4-bromoiodobenzene, 9.40 g (8.14 mmol) of tetrakis(triphenylphosphine)palladium(0), 1.2 L of toluene and 600 mL of aqueous solution of 2M sodium carbonate were added together, and stirred at 90 degrees C. for 20 hours. After the reaction was over, toluene was distilled away and methanol was added. Then, the precipitated solid was separated by filtration. The obtained solid was recrystallized with acetic ether and methanol and dried. 77.2 g of 2-(4-bromophenyl)naphthalene was obtained at an yield of 67%.

Workup

  1. distillationwas distilled away
  2. additionmethanol was added
  3. customThen, the precipitated solid was separated by filtration
  4. customThe obtained solid was recrystallized with acetic ether and methanol
  5. customdried

Sources & evidence

ORD record
ord-6970a0c67d0a48769a4d2f17297518d2
Source dataset
uspto-grants-2013_10
Patent number
US08568903B2

Reaction notes

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