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Dimethylamine → 4-Bromo-2-(dimethylaminomethyl)-1-fluorobenzene

HRID 1066841
Notes
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Reaction equation

HRID 1066841 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][NH:12][CH3:13]>CO>[CH3:11][N:12]([CH2:4][C:3]1[CH:6]=[C:7]([Br:10])[CH:8]=[CH:9][C:2]=1[F:1])[CH3:13]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 674DimethylamineHCID 135532954-Bromo-2-(bromomethyl)-1-fluorobenzene

Product 1

HCID 211961754-Bromo-2-(dimethylaminomethyl)-1-fluorobenzene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

In a 50 ml flask, under a nitrogen atmosphere, 2-fluoro-5-bromobenzyl bromide (1.264 g, 4.72 mmol) was dissolved in methanol (10 ml). Dimethylamine (8 M in H2O, 1.77 ml, 14.2 mmol) was added as a solution in methanol (5 ml), and the resulting mixture was stirred at ambient temperature for about two hours. The progress of the reaction was monitored by thin layer chromatography. The methanol was removed by evaporation. The residue was partitioned between 1 M potassium carbonate and diethyl ether. The aqueous fraction was back extracted with diethyl ether. The organic fractions were combined, washed with brine (7×) and dried over sodium sulfate. The solvents were removed in vacuo. The title intermediate was used without further purification.

Workup

  1. customThe methanol was removed by evaporation
  2. customThe residue was partitioned between 1 M potassium carbonate and diethyl ether
  3. extractionThe aqueous fraction was back extracted with diethyl ether
  4. washwashed with brine (7×)
  5. dry with materialdried over sodium sulfate
  6. customThe solvents were removed in vacuo
  7. customThe title intermediate was used without further purification

Sources & evidence

ORD record
ord-8d679847236e4b9daf1a1484f9bdf501
Source dataset
uspto-grants-2001_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06245761B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes