2-Bromoethanol → 2-((4-Bromophenyl)(methyl)amino)ethanol

HRID 57636Notes

Reaction equation

HRID 57636 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([NH:6][CH3:7])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:17][CH2:18][OH:19]>CN(C=O)C>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([N:6]([CH3:7])[CH2:17][CH2:18][OH:19])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 2757052Benzenamine, 4-bromo-N-methyl-

Product 1

HCID 235378902-((4-Bromophenyl)(methyl)amino)ethanolYield 19%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-bromo-N-methylaniline (700 mg, 3.76 mmol) was dissolved in DMF (20 mL), K2CO3 (1.56 g, 11.29 mmol) and 2-bromoethanol (1.41 g, 11.29 mmol) were added in. The mixture was reacted at 100° C. for 2 days. Then it was extracted by EA and brine, washed by brine, dried over Na2SO4, concentrated and purified by flash chromatography, (PE: EA=10:1 to 3:1) to give 164 mg brown oil.

Workup

  1. customThe mixture was reacted at 100° C. for 2 days
  2. extractionThen it was extracted by EA and brine
  3. washwashed by brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. custompurified by flash chromatography, (PE: EA=10:1 to 3:1)

Sources & evidence

ORD record
ord-6d589a2b258f454ab416792f893f1756
Source dataset
uspto-grants-2016_09
Patent number
US09434726B2

Reaction notes

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