Morpholine → 4-(2-Bromo-4-fluorobenzyl)morpholine

HRID 558140Notes

Reaction equation

HRID 558140 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9]Br.[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.C(N(C(C)C)CC)(C)C>C(#N)C>[Br:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][N:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 81531DiisopropylethylamineHCID 107069772-Bromo-1-(bromomethyl)-4-fluorobenzene

Product 1

HCID 510751744-(2-Bromo-4-fluorobenzyl)morpholineYield 95.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
81 °C

Procedure

Combine 2-bromo-1-bromomethyl-4-fluoro-benzene (4 g, 14.9 mmol), morpholine (2.6 mL, 29.8 mmol), and diisopropylethylamine (5.2 mL, 29.8 mmol) in acetonitrile (10.0 mL). Heat the reaction mixture at 81° C. for 2 h and cool to RT. Remove the solvent under reduced pressure. Dilute with DCM and wash with water and then aqueous saturated sodium chloride. Dry the organics over sodium sulfate. Filter and remove the solvent under reduced pressure to obtain the title compound (3.9 g, 95%). LCMS (ES) m/z 274 [M+1]+.

Workup

  1. temperaturecool to RT
  2. customRemove the solvent under reduced pressure
  3. additionDilute with DCM
  4. washwash with water
  5. dry with materialDry the organics over sodium sulfate
  6. filtrationFilter
  7. customremove the solvent under reduced pressure

Sources & evidence

ORD record
ord-d0b7435402014f4f8423aa7233a3c960
Source dataset
uspto-grants-2011_11
Patent number
US08063035B2

Reaction notes

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