Dichloromethane → 4-(2-Fluoro-4-nitrophenyl)morpholine

HRID 1417946Notes

Reaction equation

HRID 1417946 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[F:7][C:8]1[CH:9]=[C:10]([N+:15]([O-:17])=[O:16])[CH:11]=[CH:12][C:13]=1F.C(N(C(C)C)CC)(C)C.C(Cl)Cl>C(OCC)(=O)C.O>[F:7][C:8]1[CH:9]=[C:10]([N+:15]([O-:17])=[O:16])[CH:11]=[CH:12][C:13]=1[N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 1230531,2-Difluoro-4-nitrobenzene

Product 1

HCID 29054894-(2-Fluoro-4-nitrophenyl)morpholine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 19.9 g of morpholine, 28.7 g of 3,4-difluoronitrobenzene, and 14.8 g of diisopropyl ethylamine in 100 mL of ethyl acetate was heated at reflux under nitrogen for 4 h. The mixture was allowed to cool to room temperature overnight, then 100 mL of ethyl acetate, 150 mL of methylene chloride, and 150 mL of water were added, and the aqueous layer extracted with 2×50 mL of methylene chloride and 50 mL of ethyl acetate. The combined organic layers were dried (Na2SO4) to give a yellow solid. This was recrystallized from acetone-water to give a yellow solid, mp=112°-113° C.

Workup

  1. temperatureat reflux under nitrogen for 4 h
  2. extractionthe aqueous layer extracted with 2×50 mL of methylene chloride and 50 mL of ethyl acetate
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. customto give a yellow solid
  5. customThis was recrystallized from acetone-water
  6. customto give a yellow solid, mp=112°-113° C.

Sources & evidence

ORD record
ord-013af5173b8d4254a7051e2a88e14f18
Source dataset
uspto-grants-1999_03
Patent number
US05880118

Reaction notes

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