Sodium Chloride → 5'-Bromo-1,1':3',1''-terphenyl

HRID 1628363Notes

Reaction equation

HRID 1628363 reaction equation
Br[C:2]1[CH:7]=[C:6](Br)[CH:5]=[C:4]([Br:9])[C:3]=1N.[C:11]1([Mg]Br)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[Cl-].[Na+]>C1COCC1>[Br:9][C:4]1[CH:5]=[C:6]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:7]=[C:2]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 89862,4,6-Tribromoaniline2×HCID 178418255HCID 178418255, compound2×

Product 1

HCID 100702575'-Bromo-1,1':3',1''-terphenyl

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

10 g (0.023 mol) of 2,4,6-tribromophenylamine are dissolved in 100 ml of THF. In a second apparatus, 228 ml of phenylmagnesium bromide is heated under reflux. The dissolved 2,4,6-tribromophenylamine is added dropwise to the phenylmagnesium bromide solution, stirred under reflux for 1 h and at room temperature for a further 12 h. After addition of saturated sodium chloride solution, the aqueous phase is washed with diethyl ether and dried over sodium sulfate. After removal of the solvent, the product is recrystallised in hexane/dichloromethane. 4.8 g (77%) of clean substance are isolated.

Workup

  1. temperatureunder reflux
  2. washthe aqueous phase is washed with diethyl ether
  3. dry with materialdried over sodium sulfate
  4. customAfter removal of the solvent
  5. customthe product is recrystallised in hexane/dichloromethane
  6. custom4.8 g (77%) of clean substance are isolated

Sources & evidence

ORD record
ord-3e0853f3e0e94332b62ca79183758660
Source dataset
uspto-grants-2014_07
Patent number
US08786181B2

Reaction notes

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