Sodium Carbonate → HCID 67301191, compound

HRID 1014907Notes

Reaction equation

HRID 1014907 reaction equation
[C:1]1([C:11]2[CH:20]=[CH:19][C:18]3[C:13](=[CH:14][CH:15]=[C:16](B(O)O)[CH:17]=3)[CH:12]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Br:24][C:25]1[CH:30]=[CH:29][C:28](I)=[CH:27][CH:26]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[Br:24][C:25]1[CH:30]=[CH:29][C:28]([C:16]2[CH:15]=[CH:14][C:13]3[C:18](=[CH:19][CH:20]=[C:11]([C:1]4[C:10]5[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=5)[CH:4]=[CH:3][CH:2]=4)[CH:12]=3)[CH:17]=2)=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 115221-Bromo-4-iodobenzeneHCID 57539849HCID 57539849, compound

Product 1

HCID 67301191HCID 67301191, compoundYield 88.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Under the atmosphere of argon, 3.2 g of 2-(naphthalen-1-yl)naphthalene-6-boronic acid and 2.8 g of 4-bromoiodobenzene were dissolved into 30 ml of toluene, and 0.23 g of tetrakis(triphenyl-phosphine)palladium was added to the obtained solution. After 28 ml of a 2 M aqueous solution of sodium carbonate was added, the resultant mixture was heated under the refluxing condition for 8.5 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: toluene), and 3.6 g of 2-(4-bromophenyl)-6-(naphthalen-1-yl)naphthalene was obtained as a light yellow solid substance (the yield: 83%).

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-789a1b0e8bf3489c8dff1d8e125f9d6c
Source dataset
uspto-grants-2011_07
Patent number
US07985491B2

Reaction notes

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