Water → 4-(4-Bromophenyl)morpholine

HRID 1743183Notes

Reaction equation

HRID 1743183 reaction equation
[Br:1]Br.[N:3]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.O>C(O)C>[Br:1][C:12]1[CH:13]=[CH:14][C:9]([N:3]2[CH2:8][CH2:7][O:6][CH2:5][CH2:4]2)=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24408BromineHCID 623394-Phenylmorpholine

Product 1

HCID 116228514-(4-Bromophenyl)morpholineYield 72.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Bromine (10.8 g, 67.4 mmol) was added to a solution of 4-(4-morpholinyl)benzene (10.0 g, 61.3 mmol) in ethanol (100 mL) at 0° C., and the mixture was stirred for 1 hour at room temperature. Water (100 mL) was poured into the reaction mixture, which was then extracted twice with ethyl acetate. The organic layers were combined, washed with an aqueous saturated sodium hydrogencarbonate and water, then dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was crystallized from ethyl acetate-hexane to obtain the title compound (10.7 g, yield 72%).

Workup

  1. extractionwas then extracted twice with ethyl acetate
  2. washwashed with an aqueous saturated sodium hydrogencarbonate and water
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-dcfabafd95c54d4eaa3a8e23548d0a6b
Source dataset
uspto-grants-2006_03
Patent number
US07008950B1

Reaction notes

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