Sodium borohydride → 1-(3-Bromophenyl)-2-((2,4-dichlorobenzyl)(methyl)amino)ethanol

HRID 1470069노트

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HRID 1470069 반응식
[Cl:1][C:2]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:3]=1[CH2:4][N:5]([CH3:16])[CH2:6][C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Br:15])[CH:10]=1)=[O:8].[BH4-].[Na+]>CO>[Br:15][C:11]1[CH:10]=[C:9]([CH:7]([OH:8])[CH2:6][N:5]([CH2:4][C:3]2[CH:17]=[CH:18][C:19]([Cl:21])=[CH:20][C:2]=2[Cl:1])[CH3:16])[CH:14]=[CH:13][CH:12]=1

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 674555871-(3-Bromophenyl)-2-((2,4-dichlorobenzyl)(methyl)amino)ethanone

생성물 1

HCID 674600281-(3-Bromophenyl)-2-((2,4-dichlorobenzyl)(methyl)amino)ethanol

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
0 °C

실험 절차

Into a 1 L 3-necked round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 2-((2,4-dichlorobenzyl)(methyl)amino)-1-(3-bromophenyl)ethanone (77 g, 198.97 mmol, 1.00 equiv, theoretical yield) in methanol (300 mL). This was followed by the addition of NaBH4 (15 g, 394.74 mmol, 1.98 equiv) in several batches at 0° C. The resulting solution was stirred for 30 min at 0° C. in a water/ice bath. The reaction was then quenched by the addition of 100 mL of acetone. The resulting mixture was concentrated under vacuum. The resulting solution was extracted with 3×100 mL of ethyl acetate and the organic layers combined and dried over anhydrous sodium sulfate. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1:100). This resulted in 50 g (65%) of 2-((2,4-dichlorobenzyl)(methyl)amino)-1-(3-bromophenyl)ethanol as a yellow oil.

후처리

  1. customInto a 1 L 3-necked round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. customThe reaction was then quenched by the addition of 100 mL of acetone
  4. concentrationThe resulting mixture was concentrated under vacuum
  5. extractionThe resulting solution was extracted with 3×100 mL of ethyl acetate
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThis resulted in 50 g (65%) of 2-((2,4-dichlorobenzyl)(methyl)amino)-1-(3-bromophenyl)ethanol as a yellow oil

출처 및 근거

ORD 기록
ord-c6d4784ac220455f95356413299d036b
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09006281B2

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