4-Bromoaniline → 4-Bromo-N,N-bis(trimethylsilyl)aniline

HRID 460495Notes

Reaction equation

HRID 460495 reaction equation
NC1C=CC(B(O)O)=CC=1.[Br:11][C:12]1[CH:18]=[CH:17][C:15]([NH2:16])=[CH:14][CH:13]=1.FC(F)(F)S(O[Si:25]([CH3:28])([CH3:27])[CH3:26])(=O)=O>C(N(CC)CC)C>[CH3:26][Si:25]([CH3:28])([CH3:27])[N:16]([Si:25]([CH3:28])([CH3:27])[CH3:26])[C:15]1[CH:17]=[CH:18][C:12]([Br:11])=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 78074-BromoanilineHCID 65367Trimethylsilyl triflateHCID 27346154-Aminophenylboronic acid

Product 1

HCID 40926204-Bromo-N,N-bis(trimethylsilyl)anilineYield 65%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

4-Aminophenylboronic acid by Grignard reaction on N,N-bis(trimethylsilyl)-4-bromoaniline 10.0 g (58.1 mmol) of 4-bromoaniline were dissolved in 200 ml of triethylamine and admixed with 25 ml (130 mmol) of trimethylsilyl trifluoromethanesulfonate. The mixture was heated to reflux for 8 h. The reaction mixture was concentrated and the crude product distilled under high vacuum. 11.9 g (37.8 mmol, 65%) of N,N-bis(trimethylsilyl)-4-bromoaniline were obtained.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 8 h
  3. concentrationThe reaction mixture was concentrated
  4. distillationthe crude product distilled under high vacuum

Sources & evidence

ORD record
ord-c66d1fd4d8794bdbb6790d43a2945b72
Source dataset
uspto-grants-2007_03
Patent number
US07196219B2

Reaction notes

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