Sodium Carbonate → 1,1'-Biphenyl, 3,5-dibromo-

HRID 339424Notes

Reaction equation

HRID 339424 reaction equation
B([O-])([O-])O[C:3]1[CH:8]=[C:7]([Br:9])[CH:6]=[C:5]([Br:10])[CH:4]=1.I[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+]>O.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>[Br:10][C:5]1[CH:4]=[C:3]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:8]=[C:7]([Br:9])[CH:6]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 11575IodobenzeneHCID 86613734HCID 86613734, compound

Product 1

HCID 30149331,1'-Biphenyl, 3,5-dibromo-Yield 75%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

Suspended in 32 ml of 1,2-dimethoxymethane were 3.0 g (11 mmol) of 3,5-dibromophenyl borate, 2.2 g (11 mmol) of iodobenzene and 0.25 g (0.21 mmol) of tetrakis(triphenylphosphine)palladium, and a solution prepared by dissolving 3.4 g (32 mmol) of sodium carbonate in 16 ml of water was added thereto and refluxed for 9 hours under argon atmosphere by heating. The reaction solution was separated into two layers, and then the organic layer separated was washed in order with 5% sodium carbonate, 5% hydrochloric acid, water and saturated brine and dried on anhydrous sodium sulfate. After the organic solvent was distilled off under reduced pressure, the residue was refined by silica gel chromatography (only hexane) to obtain 2.5 g (yield: 75%) of 3,5-dibromobiphenyl (5).

Workup

  1. customa solution prepared
  2. additionwas added
  3. temperaturerefluxed for 9 hours under argon atmosphere
  4. temperatureby heating
  5. customThe reaction solution was separated into two layers
  6. customthe organic layer separated
  7. washwas washed in order with 5% sodium carbonate, 5% hydrochloric acid, water and saturated brine
  8. dry with materialdried on anhydrous sodium sulfate
  9. distillationAfter the organic solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-d027abda632343ce85d845f123177256
Source dataset
uspto-grants-2014_11
Patent number
US08895154B2

Reaction notes

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