Bis(2-bromoethyl) ether → 1-(2-Fluoro-5-morpholin-4-yl-phenyl)ethanone

HRID 2307429Notes

Reaction equation

HRID 2307429 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([F:11])=[C:6]([C:8](=[O:10])[CH3:9])[CH:7]=1.Br[CH2:13][CH2:14][O:15][CH2:16][CH2:17]Br.CCN(C(C)C)C(C)C>C1(C)C=CC=CC=1>[F:11][C:5]1[CH:4]=[CH:3][C:2]([N:1]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:7][C:6]=1[C:8](=[O:10])[CH3:9]

Participants

5

Reactant 3

HCID 21521Bis(2-bromoethyl) etherHCID 81531DiisopropylethylamineHCID 27811251-(5-Amino-2-fluorophenyl)ethanone

Product 1

HCID 226054681-(2-Fluoro-5-morpholin-4-yl-phenyl)ethanoneYield 73.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 1-(5-amino-2-fluoro-phenyl)-ethanone (3.5 g), bromoethyl ether (5.929 g), and i-Pr2NEt (7.121 g) in toluene (20 mL) was refluxed for 16 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 residue was purified by silica gel flash chromatography (25% ethyl acetate in hexane) to give 3.74 g of the title compound as an oil.

Workup

  1. temperaturewas refluxed for 16 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 residue was purified by silica gel flash chromatography (25% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-741a641706fa49c083d8dcf5d9da262f
Source dataset
uspto-grants-2004_12
Patent number
US06831080B2

Reaction notes

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