Ethanolamine → (RS)-1-(4-bromo-2-fluorophenyl)-2-(2-hydroxyethylamino)ethanol

HRID 2403330Notes

Reaction equation

HRID 2403330 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:10][O:9]2)=[C:4]([F:11])[CH:3]=1.[NH2:12][CH2:13][CH2:14][OH:15].CCOC(C)=O.C1COCC1>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:9])[CH2:10][NH:12][CH2:13][CH2:14][OH:15])=[C:4]([F:11])[CH:3]=1

Participants

5

Reactant 3

HCID 700EthanolamineHCID 21939870Tetrahydrofuran ethyl acetateHCID 627729372-(4-Bromo-2-fluorophenyl)oxirane

Product 1

HCID 68325594(RS)-1-(4-bromo-2-fluorophenyl)-2-(2-hydroxyethylamino)ethanolYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (RS)-2-(4-bromo-2-fluorophenyl)oxirane (12.3 g) in THF (40 ml) was added 2-aminoethanol (33.9 ml) and the mixture was stirred at room temperature overnight. The reaction mixture was then poured into EtOAc/THF (3:1) and washed with saturated brine. The organic layer was separated, dried over Na2SO4 and concentrated in vacuo. The crude product was purified by flash chromatography (silica gel; gradient: 0% to 35% MeOH in dichloromethane containing a few drops of aq. NH3) to afford (RS)-1-(4-bromo-2-fluorophenyl)-2-(2-hydroxyethylamino)ethanol (12.0 g, 76%) as a brown oil. MS (ISP): 280.0 ([{81Br}M+H]−), 278.0 ([{79Br}M+H]+).

Workup

  1. washwashed with saturated brine
  2. customThe organic layer was separated
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by flash chromatography (silica gel; gradient: 0% to 35% MeOH in dichloromethane containing a few drops of aq. NH3)

Sources & evidence

ORD record
ord-95b01701168447d092ee49a15ad87fa6
Source dataset
uspto-grants-2014_08
Patent number
US08802673B2

Reaction notes

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