Toluene → HCID 57539839, compound

HRID 1014906Notes

Reaction equation

HRID 1014906 reaction equation
[C:1]1([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](B(O)O)=[CH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:20][C:21]1[CH:22]=[C:23](I)[CH:24]=[CH:25][CH:26]=1.C1(C)C=CC=CC=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.COCCOC>[Br:20][C:21]1[CH:22]=[C:23]([C:10]2[C:11]3[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=3)[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:8][CH:9]=2)[CH:24]=[CH:25][CH:26]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 11561Benzene, 1-bromo-3-iodo-HCID 45382260(4-Phenylnaphthalen-1-yl)boronic acid

Product 1

HCID 57539839HCID 57539839, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

Under the atmosphere of argon, 11.6 g of 1-phenylnaphthalene-4-boronic acid and 14.5 g of 3-bromoiodobenzene were dissolved into 160 ml of toluene and 30 ml of DME, and 1.79 g of tetrakis(triphenylphosphine)palladium was added to the obtained solution. After 90 ml of a 2 M aqueous solution of sodium carbonate was added, the resultant mixture was heated under the refluxing condition for 8 hours. After the obtained mixture was left standing for one night, the mixture was subjected to extraction with toluene. The extract was washed with a saturated aqueous solution of sodium chloride, and the solvent was removed using an evaporator. The residue was purified in accordance with the silica gel column chromatography (the developing solvent: hexane/toluene=5/1), and 10.4 g of 1-(3-bromophenyl)-4-phenylnaphthalene was obtained as white crystals (the yield: 62%).

Workup

  1. additionwas added to the obtained solution
  2. waitAfter the obtained mixture was left
  3. waitstanding for one night
  4. extractionthe mixture was subjected to extraction with toluene
  5. washThe extract was washed with a saturated aqueous solution of sodium chloride
  6. customthe solvent was removed
  7. customan evaporator
  8. customThe residue was purified in accordance with the silica gel column chromatography (the developing solvent

Sources & evidence

ORD record
ord-aab5b4e2e11b40e4b6269ae8f09a2583
Source dataset
uspto-grants-2011_07
Patent number
US07985491B2

Reaction notes

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