Bis(2-bromoethyl) ether → 2,2,2-Trifluoro-1-(3-morpholin-4-yl-phenyl)-ethanone oxime

HRID 2307424Notes

Reaction equation

HRID 2307424 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8](=[N:13][OH:14])[C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:6][CH:7]=1.Br[CH2:16][CH2:17][O:18][CH2:19][CH2:20]Br.CCN(C(C)C)C(C)C>C1(C)C=CC=CC=1>[F:10][C:9]([F:12])([F:11])[C:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([N:1]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[CH:3]=1)=[N:13][OH:14]

Participants

5

Reactant 3

HCID 21521Bis(2-bromoethyl) etherHCID 81531DiisopropylethylamineHCID 739856931-(3-Aminophenyl)-2,2,2-trifluoroethanone oxime

Product 1

HCID 739856882,2,2-Trifluoro-1-(3-morpholin-4-yl-phenyl)-ethanone oximeYield 89.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 1-(3-aminophenyl)-2,2,2-trifluoroethanone oxime (1.7 g), bromoethyl ether (2.246 g), and i-Pr2NEt (2.57 g) in toluene (20 mL) was refluxed for 4 hours. After cooling, the reaction mixture was quenched with water. The aqueous layer was extracted with dichloromethane, and the combined organic layers were dried over magnesium sulphate, filtered and concentrated in vacuo. The crude product was purified by silica gel flash chromatography (50% ethyl acetate in hexane) to give the title compound as an oil (2.04 g).

Workup

  1. temperaturewas refluxed for 4 hours
  2. temperatureAfter cooling
  3. customthe reaction mixture was quenched with water
  4. extractionThe aqueous layer was extracted with dichloromethane
  5. dry with materialthe combined organic layers were dried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by silica gel flash chromatography (50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-5c57a140ed5342678bcecd7b8bbc7fd2
Source dataset
uspto-grants-2004_12
Patent number
US06831080B2

Reaction notes

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