Sodium Carbonate → HCID 23139677, compound

HRID 534810Notes

Reaction equation

HRID 534810 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Br:12])[CH:8]=2)[CH:3]=1.[C:13]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:14](B(O)O)=[CH:15][CH:16]=[CH:17][CH:18]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[C:13]1([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=1[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([Br:12])[CH:8]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 6405912,6-DibromonaphthaleneHCID 4589187Biphenyl-2-boronic acid

Product 1

HCID 23139677HCID 23139677, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The procedure of Synthesis Example 1 was repeated except that 2-naphthalene boronic acid in place of phenylboronic acid was used, and then 7.5 g of 1-bromo-4-(naphthalene-2-yl)naphthalene of white crystal was obtained (yield: 43%). Synthesis Example 3 (Synthesis of 2-(biphenyl-2-yl)-6-bromonaphthelene) 15 g of 2,6-dibromonaphthalene on the market, 12.5 g of 2-biphenylboronic acid and 1.8 g of tetrakis(triphenylphophine)palladium were mixed, followed by argon displacement. After adding 250 ml of toluene and 90 ml of 2M sodium carbonate aqueous solution thereto, it was refluxed on heating for 7 hours. After standing to cool, the organic layer was extracted by toluene, and then it was washed by water and saturated salt water. Subsequently the organic layer was dried by using sodium sulfate anhydride, and then the solvent was removed by distillation. The product was refined through a silica gel chromatography and then 10.9 g of 2-(biphenyl-2-yl)-6-bromonaphthalene of white crystal was obtained (yield: 58%).

Workup

  1. additionwere mixed
  2. temperatureit was refluxed
  3. temperatureon heating for 7 hours
  4. temperatureto cool
  5. extractionthe organic layer was extracted by toluene
  6. washit was washed by water and saturated salt water
  7. customSubsequently the organic layer was dried
  8. customthe solvent was removed by distillation

Sources & evidence

ORD record
ord-8d384095560e4fb78e445c2b078ed672
Source dataset
uspto-grants-2014_10
Patent number
US08853675B2

Reaction notes

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