Morpholine → 1-(4-Bromo-3-fluorophenyl)-2-(4-morpholinyl)ethanone

HRID 2114441Notes

Reaction equation

HRID 2114441 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([Br:11])=[C:7]([F:12])[CH:6]=1)=[O:4].[NH:13]1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1>C1COCC1.ClCCl>[Br:11][C:8]1[CH:9]=[CH:10][C:5]([C:3](=[O:4])[CH2:2][N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[CH:6][C:7]=1[F:12]

Participants

5

Reactant 2

HCID 8083MorpholineHCID 534166144-Bromo-3-fluorophenacyl bromide

Product 1

HCID 574186821-(4-Bromo-3-fluorophenyl)-2-(4-morpholinyl)ethanone

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a 0° C. solution containing 0.55 g of 2-bromo-1-(4-bromo-3-fluorophenyl)ethanone (1.86 mmols) in 9 mL of THF was added 0.32 mL of morpholine (3.72 mmols). After 18 h the reaction mixture was diluted with 100 mL of dichloromethane and washed with water (1×10 mL) and saturated brine solution (1×10 mL). The organic layer was dried over MgSO4, filtered through a frit, and concentrated to a yellow-orange oil which was used without further purification. MS (ES) m/e 302, 303 [M+H]+.

Workup

  1. washwashed with water (1×10 mL) and saturated brine solution (1×10 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered through a frit
  4. concentrationconcentrated to a yellow-orange oil which
  5. customwas used without further purification

Sources & evidence

ORD record
ord-88c9c43cae7743199c33050ca23c57d6
Source dataset
uspto-grants-2008_10
Patent number
US07432258B2

Reaction notes

Loading…