Sodium Carbonate → 2-(Biphenyl-2-yl)-6-bromonaphthalene

HRID 1506273Notes

Reaction equation

HRID 1506273 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+]>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>[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

6

Reactant 3

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

Product 1

HCID 231396772-(Biphenyl-2-yl)-6-bromonaphthaleneYield 58%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

15 g of 2,6-dibromonaphthalene on the market, 12.5 g of 2-biphenylboronic acid and 1.8 g of tetrakis(triphenylphosphine)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. temperatureit was refluxed
  2. temperatureon heating for 7 hours
  3. temperatureto cool
  4. extractionthe organic layer was extracted by toluene
  5. washit was washed by water and saturated salt water
  6. customSubsequently the organic layer was dried
  7. customthe solvent was removed by distillation

Sources & evidence

ORD record
ord-13625644dd1b49dd8619d0f069cad063
Source dataset
uspto-grants-2015_12
Patent number
US09219234B2

Reaction notes

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