Morpholine → 4-(3-Bromo-5-chlorophenyl)morpholine

HRID 1431759Notes

Reaction equation

HRID 1431759 reaction equation
[Br:1][C:2]1[CH:7]=[C:6](F)[CH:5]=[C:4]([Cl:9])[CH:3]=1.[NH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[C:6]([N:10]2[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)[CH:5]=[C:4]([Cl:9])[CH:3]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 27362231-Bromo-3-chloro-5-fluorobenzene

Product 1

HCID 532170884-(3-Bromo-5-chlorophenyl)morpholine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1-bromo-3-chloro-5-fluorobenzene (5.05 g, 24.11 mmol), morpholine (3.15 mL, 36.2 mmol), potassium carbonate (6.66 g, 48.2 mmol), and DMF (45 mL) was stirred at 60° C. for 48 h, then at 110° C. for 24 h. The reaction mixture was concd, and the resulting residue was partitioned between EtOAc and water. The organic phase was dried over magnesium sulfate and concd, affording a crude material that was purified by column chromatography (silica; 0-10% EtOAc in hexanes) to yield 4-(3-bromo-5-chlorophenyl)morpholine as a white amorphous solid. Mass Spectrum (ESI) m/e=276.0 (M+1).

Workup

  1. customthe resulting residue was partitioned between EtOAc and water
  2. dry with materialThe organic phase was dried over magnesium sulfate and concd
  3. customaffording a crude material that
  4. customwas purified by column chromatography (silica; 0-10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-5d90e6a2f42947d7923c2fd5873b2b5b
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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