Ethanolamine → HCID 68325563, compound

HRID 571817Notes

Reaction equation

HRID 571817 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[Cl: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[Cl:11]

Participants

5

Reactant 2

HCID 700EthanolamineHCID 86671405HCID 86671405, compound

Product 1

HCID 68325563HCID 68325563, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a stirred solution of (RS)-2-(4-bromo-3-chlorophenyl)oxirane (15.2 g) in THF (40 ml) was added 2-aminoethanol (35.1 ml) and the mixture was stirred at room temperature for 7 hours. 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-chlorophenyl)-2-(2-hydroxyethylamino)ethanol (19.0 g) as a yellow oil which was used in the next step without further purification. MS (ISP): 298.1 ([{81Br37Cl}M+H]+), 296.0 ([{79Br37Cl/81Br35Cl}M+H]+), 293.9 ([{79Br35Cl}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-8738d9be930744f9868bd47cf144c775
Source dataset
uspto-grants-2015_05
Patent number
US09029370B2

Reaction notes

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