Water → HCID 63333977, compound

HRID 1754932Notes

Reaction equation

HRID 1754932 reaction equation
C(N(CC)CC)C.Br[CH:9]([OH:11])[CH3:10].[Br:12][C:13]1[CH:14]=[C:15]([NH2:20])[CH:16]=[CH:17][C:18]=1[CH3:19].O>C1(C)C=CC=CC=1>[Br:12][C:13]1[CH:14]=[C:15]([NH:20][CH2:10][CH2:9][OH:11])[CH:16]=[CH:17][C:18]=1[CH3:19]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 82187Benzenamine, 3-bromo-4-methyl-HCID 14202443Ethanol, 1-bromo-

Product 1

HCID 63333977HCID 63333977, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

Triethylamine (0.28 mL, 2.00 mmol) and bromoethanol (0.14 mL, 1.98 mmol) were added to a solution of 3-bromo-4-methyl-phenylamine (240 mg, 1.29 mmol) in toluene (2 ml). The mixture was stirred at 100° C. overnight and H2O was then added, followed by extraction with AcOEt (×2). The organic layers were combined and sequentially washed with H2O and saturated brine, and then dried over Na2SO4 and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (n-hexane/AcOEt) to give 2-(3-bromo-4-methyl-phenylamino)-ethanol (185 mg, 62%).

Workup

  1. extractionfollowed by extraction with AcOEt (×2)
  2. washsequentially washed with H2O and saturated brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (n-hexane/AcOEt)

Sources & evidence

ORD record
ord-df06129f810d4fa78261f028e46c3f96
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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