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

HRID 571764ノート

反応式

HRID 571764 の反応式
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

参加物

6

反応物 3

HCID 74544-Bromophenacyl bromideHCID 7504BenzylamineHCID 4311764Sodium borohydride

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 6212Chloroform溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-c510b2149b344e5b996f8e6a570d522c
出典データセット
uspto-grants-2015_05
特許番号
US09029371B2

反応ノート

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