1,4-Dibromobenzene → 4'-Bromo-N,N-dimethylbiphenylmethanamine

HRID 1900135Notes

Reaction equation

HRID 1900135 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]([Br:9])=[CH:5][CH:4]=1.Br[C:11]1[CH:20]=[CH:19][C:14]([CH2:15][N:16]([CH3:18])[CH3:17])=[CH:13][CH:12]=1>O1CCCC1.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:9][C:6]1[CH:7]=[CH:8][C:3]([C:13]2[C:14]([CH2:15][N:16]([CH3:18])[CH3:17])=[CH:19][CH:20]=[CH:11][CH:12]=2)=[CH:4][CH:5]=1

Participants

6

Reactant 3

HCID 78041,4-DibromobenzeneHCID 2357574-Bromo-N,N-dimethylbenzylamineHCID 5462224Magnesium

Product 1

HCID 190437124'-Bromo-N,N-dimethylbiphenylmethanamine

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of the Grignard reagent prepared from 344 mg of magnesium and 2.27 g of 1,4-dibromobenzene in 15 ml of THF (tetrahydrofuran) is added dropwise to a suspension of 2 g of 4-bromo-N,N-dimethylbenzylamine and 158 mg of tetrakistriphenylphosphinepalladium in 10 ml of THF. The addition is carried out at room temperature and under an argon atmosphere. After completion of the addition, the mixture is heated to boiling for an additional 5 hours and then evaporated under reduced pressure. The residue is then treated with ether and saturated ammonium chloride solution and the aqueous phase is separated. This is extracted with ether. The organic extracts are washed with saturated sodium chloride solution, dried over magnesium sulfate and evaporated. The residue is purified by chromatography on silica gel while eluting with methylene chloride/methanol 9:1. 4'-Bromo-N,N-dimethylbiphenylmethanamine, m.p. 60°-62°C., is obtained.

Workup

  1. additionThe addition
  2. customis carried out at room temperature and under an argon atmosphere
  3. additionAfter completion of the addition
  4. temperaturethe mixture is heated
  5. customevaporated under reduced pressure
  6. additionThe residue is then treated with ether and saturated ammonium chloride solution
  7. customthe aqueous phase is separated
  8. extractionThis is extracted with ether
  9. washThe organic extracts are washed with saturated sodium chloride solution
  10. dry with materialdried over magnesium sulfate
  11. customevaporated
  12. customThe residue is purified by chromatography on silica gel
  13. washwhile eluting with methylene chloride/methanol 9:1

Sources & evidence

ORD record
ord-3d646cab63ee43a7ac97e2ba15c41229
Source dataset
uspto-grants-1996_11
Patent number
US05574071

Reaction notes

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