Ethanolamine → (RS)-1-(4-bromo-3-fluoro-phenyl)-2-(2-hydroxy-ethylamino)-ethanol

HRID 2403297Notes

Reaction equation

HRID 2403297 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:10][O:9]2)=[CH:4][C:3]=1[F:11].[NH2:12][CH2:13][CH2:14][OH:15]>C1COCC1.[Cl-].[Na+].O>[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])=[CH:4][C:3]=1[F:11]

Participants

5

Reactant 2

HCID 700EthanolamineHCID 814417622-(4-Bromo-3-fluorophenyl)oxirane

Product 1

HCID 68325495(RS)-1-(4-bromo-3-fluoro-phenyl)-2-(2-hydroxy-ethylamino)-ethanol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a stirred solution of (RS)-2-(4-bromo-3-fluoro-phenyl)-oxirane (4.69 g) in THF (11 ml) was added 2-aminoethanol (13.2 ml) and the mixture was stirred at room temperature overnight. The reaction mixture was then poured into brine and extracted twice with EtOAc. The combined organic layers was dried over Na2SO4 and concentrated in vacuo to afford (RS)-1-(4-bromo-3-fluoro-phenyl)-2-(2-hydroxy-ethylamino)-ethanol (5.37 g) as a yellow viscous oil which was used in the next step without further purification. MS (ISP): 280.2 ([{81Br}M+H]+), 278.1 ([{79Br}M+H]+).

Workup

  1. extractionextracted twice with EtOAc
  2. dry with materialThe combined organic layers was dried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cd4444e65e2f4db9a9d70a2bae1c5fa9
Source dataset
uspto-grants-2014_08
Patent number
US08802673B2

Reaction notes

Loading…