Toluene → HCID 23110736, compound

HRID 1662909Notes

Reaction equation

HRID 1662909 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[C:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:18]([Br:25])=[CH:17][CH:16]=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.C(COC)OC>[Br:25][C:18]1[C:19]2[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:15]([C:3]2[CH:2]=[CH:1][C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=2)=[CH:16][CH:17]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 665211,4-DibromonaphthaleneHCID 2734375(Naphthalen-2-yl)boronic acid

Product 1

HCID 23110736HCID 23110736, compoundYield 25.3%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
78 °C

Procedure

Under an argon gas atmosphere, 121 g (700 mmol) of 2-naphthaleneboronic acid, 200.0 g (700 mmol) of 1,4-dibromonaphthalene, 16.2 g (13.4 mmol) of tetrakis(triphenylphosphine) palladium(0), 3.0L of toluene, 3.2L of dimethoxyethane and 1.60L of 2M sodium carbonate solution were mixed, and stirred for 20 hours at 78 degrees C. The reaction mixture experienced filtration to be subsequently cleansed by water and methanol. The obtained solid was added with toluene to be heat-dissolved. Insoluble matter therein was eliminated by filtration, such that the filtrate was distilled away under reduced pressure. By recrystallizing residue by toluene and hexane, 59 g of 4-bromo-1-(2-naphthyl)naphthalene was obtained at an yield of 25%.

Workup

  1. filtrationfiltration
  2. additionThe obtained solid was added with toluene
  3. dissolutionto be heat-dissolved
  4. filtrationInsoluble matter therein was eliminated by filtration, such that the filtrate
  5. distillationwas distilled away under reduced pressure
  6. customBy recrystallizing residue by toluene and hexane

Sources & evidence

ORD record
ord-5ff77ae854f54163988156824c1b5af5
Source dataset
uspto-grants-2011_10
Patent number
US08034256B2

Reaction notes

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