Methylamine → 1-(5-Bromo-2-fluorophenyl)-N-methylmethanamine

HRID 1066843Notes

Reaction equation

HRID 1066843 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][C:3]=1[CH2:4]Br.[CH3:11][NH2:12]>CO>[CH3:11][NH:12][CH2:4][C:3]1[CH:6]=[C:7]([Br:10])[CH:8]=[CH:9][C:2]=1[F:1]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 135532954-Bromo-2-(bromomethyl)-1-fluorobenzene

Product 1

HCID 167739911-(5-Bromo-2-fluorophenyl)-N-methylmethanamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a 25 ml flask, under a nitrogen atmosphere, 2-fluoro-5-bromobenzylbromide (755 mg, 2.82 mmol) was dissolved in methanol (10 ml). Methylamine (0.99 ml, 14.1 mmol) was added and the mixture was stirred at ambient temperature for about three hours. The progress of the reaction was monitored by thin layer chromatography. The solvents were removed by evaporation. The residue was partitioned between 1 M potassium carbonate and methylene chloride. The aqueous fraction was back extracted with methylene chloride. The organic fractions were combined and dried over sodium sulfate. The solvents were removed in vacuo. The title intermediate was further purified by liquid chromatography.

Workup

  1. customThe solvents were removed by evaporation
  2. customThe residue was partitioned between 1 M potassium carbonate and methylene chloride
  3. extractionThe aqueous fraction was back extracted with methylene chloride
  4. dry with materialdried over sodium sulfate
  5. customThe solvents were removed in vacuo
  6. customThe title intermediate was further purified by liquid chromatography

Sources & evidence

ORD record
ord-78498e19d24d4d07a5450b17c2b49d34
Source dataset
uspto-grants-2001_06
Patent number
US06245761B1

Reaction notes

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