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

HRID 1470069Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1470069
[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

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-c6d4784ac220455f95356413299d036b
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09006281B2

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