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

HRID 1479334Notes

Reaction equation

HRID 1479334 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d17b1f28a1d748c78f2745c7078d5325
Source dataset
uspto-grants-2016_08
Patent number
US09408840B2

Reaction notes

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