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

HRID 710251Notes

Reaction equation

HRID 710251 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].O1CCCC1.[CH2:17]([CH2:19][NH2:20])[OH:18]>[Cl-].[Na+].O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:9])[CH2:10][NH:20][CH2:19][CH2:17][OH:18])=[CH:4][C:3]=1[F:11]

Participants

5

Reactant 3

HCID 700EthanolamineHCID 8028TetrahydrofuranHCID 814417622-(4-Bromo-3-fluorophenyl)oxirane

Product 1

HCID 68325495(RS)-1-(4-bromo-3-fluoro-phenyl)-2-(2-hydroxy-ethylamino)-ethanolYield 92%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

2-(4-Bromo-3-fluoro-phenyl)-oxirane (25.1 g, 109 mmol) was combined with tetrahydrofurane (70 ml) to give a yellow solution. Ethanolamine (66.4 g, 65.1 ml, 1.09 mol) was added. The resulting orange solution was stirred at room temperature overnight. The reaction mixture was poured into brine and extracted twice with ethyl acetate. The organic layers were dried over MgSO4 and concentrated in vacuo to yield a yellow oil (27.9 g, 92%), MS (ISP): 277.9 ([{79Br}M+H]+), 279.9 ([{81Br}M+H]+).

Workup

  1. customto give a yellow solution
  2. extractionextracted twice with ethyl acetate
  3. dry with materialThe organic layers were dried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3391b096f3694ce68d14da5e64cbb68b
Source dataset
uspto-grants-2015_11
Patent number
US09181230B2

Reaction notes

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