4-Bromophenacyl bromide → 2-Benzylamino-1-(4-bromo-phenyl)-ethanol

HRID 571764Notes

Reaction equation

HRID 571764 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][CH:6]=1)=[O:4].[CH2:12]([NH2:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[BH4-].[Na+]>CCO.C(Cl)(Cl)Cl>[CH2:12]([NH:19][CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[CH:7][CH:6]=1)[OH:4])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 3

HCID 74544-Bromophenacyl bromideHCID 7504BenzylamineHCID 4311764Sodium borohydride

Product 1

HCID 580978892-Benzylamino-1-(4-bromo-phenyl)-ethanolYield 43.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6212ChloroformSolvent

Procedure

To a cooled (0° C.) suspension of 2-bromo-1-(4-bromophenyl)ethanone (40.24 g; 0.14 mol) in EtOH (500 mL) and CHCl3 (100 mL) was added benzylamine (63 mL; 0.58 mol). After 30 minutes the ice-bath was removed and the mixture stirred for another 2 hours at RT. Subsequently the reaction mixture was cooled again to 0° C. and NaBH4 (6.26 g; 165.5 mmol) was added in small portions. The resulting mixture was stirred at 0° C. for 1 hour and thereafter another 4 hours at RT. The reaction mixture was quenched with 1M aqueous HCl (750 mL) at 0° C. and stirred at RT for 1 hour. The reaction mixture was concentrated in vacuo and the residue was partitioned between EtOAc and 1M aqueous NaOH. The organic layer was dried (Na2SO4), filtered, concentrated in vacuo. The residue was crystallized from tert-butyl methyl ether/heptanes to afford 2-benzylamino-1-(4-bromo-phenyl)-ethanol (18.8 g).

Workup

  1. temperatureTo a cooled
  2. customAfter 30 minutes the ice-bath was removed
  3. temperatureSubsequently the reaction mixture was cooled again to 0° C.
  4. stirringThe resulting mixture was stirred at 0° C. for 1 hour
  5. customanother 4 hours
  6. customat RT
  7. customThe reaction mixture was quenched with 1M aqueous HCl (750 mL) at 0° C.
  8. stirringstirred at RT for 1 hour
  9. concentrationThe reaction mixture was concentrated in vacuo
  10. customthe residue was partitioned between EtOAc and 1M aqueous NaOH
  11. dry with materialThe organic layer was dried (Na2SO4)
  12. filtrationfiltered
  13. concentrationconcentrated in vacuo
  14. customThe residue was crystallized from tert-butyl methyl ether/heptanes

Sources & evidence

ORD record
ord-c510b2149b344e5b996f8e6a570d522c
Source dataset
uspto-grants-2015_05
Patent number
US09029371B2

Reaction notes

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