Allyl bromide → HCID 20222783, compound

HRID 979799Notes

Reaction equation

HRID 979799 reaction equation
C([Mg]Br)C.[CH3:5][NH:6][C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][CH:8]=1.[CH2:14](Br)[CH:15]=[CH2:16].[Cl-].[NH4+]>CCOCC>[CH3:5][N:6]([CH2:16][CH:15]=[CH2:14])[C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][CH:8]=1

Participants

6

Reactant 4

HCID 7841Allyl bromideHCID 25517Ammonium ChlorideHCID 2757052Benzenamine, 4-bromo-N-methyl-HCID 178418443HCID 178418443, compound2×

Product 1

HCID 20222783HCID 20222783, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

280 ml of a solution of ethyl magnesium bromide in ether were added dropwise at less than 20° C. under an inert atmosphere to 50.05 g of N-methyl-4-bromo-aniline and after stirring for 30 minutes, 28 ml of allyl bromide were added thereto over 15 minutes. The mixture was refluxed for 40 minutes and was allowed to cool. 25 ml of a solution N of ethyl magnesium bromide in ether were added thereto dropwise and the mixture was stirred for 25 minutes and poured into iced ammonium chloride solution. The decanted aqueous phase was extracted with methylene chloride and the organic phase was dried and evaporated to dryness to obtain 61.35 g of N-methyl-N-allyl-4-bromo-aniline.

Workup

  1. waitover 15 minutes
  2. temperatureThe mixture was refluxed for 40 minutes
  3. temperatureto cool
  4. stirringdropwise and the mixture was stirred for 25 minutes
  5. extractionThe decanted aqueous phase was extracted with methylene chloride
  6. customthe organic phase was dried
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-8e45a5ba14444c64a49e8c484b32c63b
Source dataset
uspto-grants-1987_01
Patent number
US04634695

Reaction notes

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