Imidazole → 7-Bromo-2-(1-imidazolylmethyl)-1-tetralone

HRID 280629Notes

Reaction equation

HRID 280629 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([CH2:13]N(C)C)[C:9]2=[O:12])=[CH:4][CH:3]=1.[NH:17]1[CH:21]=[CH:20][N:19]=[CH:18]1>C1(C)C(C)=CC=CC=1>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([CH2:13][C:18]3[NH:17][CH:21]=[CH:20][N:19]=3)[C:9]2=[O:12])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 136630577-Bromo-2-dimethylaminomethyl-1-tetralone

Product 1

HCID 704562717-Bromo-2-(1-imidazolylmethyl)-1-tetralone

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A solution of 7-bromo-2-dimethylaminomethyl-1-tetralone free base (6.0 g) and imidazole (2.5 g) in xylene (30 ml) was heated under reflux for 1.5 hours and then evaporated. The residue was dissolved in ether and the solution was washed with water followed by dilute hydrochloric acid. The acid extract was made just alkaline with dilute sodium hydroxide solution. The mixture was extracted with chloroform and the combined chloroform extracts were washed with water and dried (Na2SO4). Evaporation of the solvent gave a solid which was crystallised from ethyl acetate to give 7-bromo-2-(1-imidazolylmethyl)-1-tetralone, m.p. 129°-131°.

Workup

  1. temperatureunder reflux for 1.5 hours
  2. customevaporated
  3. dissolutionThe residue was dissolved in ether
  4. washthe solution was washed with water
  5. extractionThe acid extract
  6. extractionThe mixture was extracted with chloroform
  7. washthe combined chloroform extracts were washed with water
  8. dry with materialdried (Na2SO4)
  9. customEvaporation of the solvent
  10. customgave a solid which
  11. customwas crystallised from ethyl acetate

Sources & evidence

ORD record
ord-dcf20b55d9f14d3a820867fcdb2d8617
Source dataset
uspto-grants-1986_05
Patent number
US04590200

Reaction notes

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