1,3,5-Tribromobenzene → HCID 58239591, compound

HRID 1877715Notes

Reaction equation

HRID 1877715 reaction equation
Br[C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[C:4]([Br:9])[CH:3]=1.[CH2:10]([O:17][C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>O.C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:10]([O:17][C:18]1[CH:23]=[CH:22][C:21]([C:2]2[CH:7]=[C:6]([Br:8])[CH:5]=[C:4]([Br:9])[CH:3]=2)=[CH:20][CH:19]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 2

HCID 122791,3,5-TribromobenzeneHCID 27343144-Benzyloxy-phenylboronic acid

Product 1

HCID 58239591HCID 58239591, compound

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

9.0 g (32 mmol) of sodium metaborate octahydrate and 1.3 g (1.82 mmol) of bis(triphenylphosphine)palladium(II) chloride are initially introduced in 200 ml of water and 40 ml of THF, a solution of 55 g (171 mmol) of 1,3,5-tribromobenzene in 80 ml of THF is added, and a solution of 10 g (45.5 mmol) of 4-benzyloxybenzeneboronic acid is added dropwise under reflux. The batch is heated under reflux for 16 h, added to water and extracted three times with MTB ether. The combined org. phases are washed with sat. sodium chloride soln. and dried over sodium sulfate. The solvent is removed in vacuo, and the residue is chromatographed on silica gel with heptane/ethyl acetate (19:1) and recrystallised from ethanol, giving 4′-benzyloxy-3,5-dibromobiphenyl as colourless crystals.

Workup

  1. temperatureunder reflux
  2. temperatureThe batch is heated
  3. temperatureunder reflux for 16 h
  4. extractionextracted three times with MTB ether
  5. washphases are washed with sat. sodium chloride soln
  6. dry with materialand dried over sodium sulfate
  7. customThe solvent is removed in vacuo
  8. customthe residue is chromatographed on silica gel with heptane/ethyl acetate (19:1)
  9. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-431d8c588e6e472580d4f0e596917489
Source dataset
uspto-grants-2012_11
Patent number
US08313669B2

Reaction notes

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