Benzyl Bromide → HCID 58288335, compound

HRID 1476121Notes

Reaction equation

HRID 1476121 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[CH:6][C:7]([Cl:11])=[C:8]([CH:10]=1)[NH2:9].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1COCC1>[CH2:12]([N:9]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:8]1[CH:10]=[C:4]([Br:3])[CH:5]=[CH:6][C:7]=1[Cl:11])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 38307312-Chloro-5-bromoaniline

Product 1

HCID 58288335HCID 58288335, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
0 °C

Procedure

Under argon, 9.69 g (242.16 mmol, 60% in mineral oil) of sodium hydride were suspended in 100 ml of THF, and the mixture was cooled to 0° C. 20.0 g (96.86 mmol) of 5-bromo-2-chloroaniline, dissolved in 50 ml of THF, were then slowly added dropwise, and the mixture was stirred at 0° C. for 30 min 39.76 g (232.47 mmol) of benzyl bromide, dissolved in 150 ml of THF, were then slowly added to the reaction mixture, and the mixture was then warmed to room temperature. The mixture was stirred at RT overnight and then carefully poured onto 150 ml of ice-water. The organic phase was separated off, and the aqueous phase was then extracted three more times with ethyl acetate. The combined organic phases were dried over sodium sulphate. After filtration, the solvent was removed under reduced pressure. Isopropanol was added to the crude product obtained, and the crystals formed were filtered off with suction and dried at 40° C. under high vacuum. This gave 14 g of the title compound. The filtrate was evaporated and the residue obtained was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 20:1). This gave a further 7.57 g of the title compound (total yield: 21.57 g, 58% of theory).

Workup

  1. additionwere then slowly added dropwise
  2. additionwere then slowly added to the reaction mixture
  3. temperaturethe mixture was then warmed to room temperature
  4. customThe organic phase was separated off
  5. extractionthe aqueous phase was then extracted three more times with ethyl acetate
  6. dry with materialThe combined organic phases were dried over sodium sulphate
  7. filtrationAfter filtration
  8. customthe solvent was removed under reduced pressure
  9. additionIsopropanol was added to the crude product
  10. customobtained
  11. customthe crystals formed
  12. filtrationwere filtered off with suction
  13. customdried at 40° C. under high vacuum
  14. customThe filtrate was evaporated
  15. customthe residue obtained
  16. customwas purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 20:1)

Sources & evidence

ORD record
ord-0a2eee8788b9498ca27199b7da124d03
Source dataset
uspto-grants-2015_04
Patent number
US09018414B2

Reaction notes

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