Morpholine → 4-(2-Fluoro-5-vinyl-phenyl)-morpholine

HRID 1825041Notes

Reaction equation

HRID 1825041 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH:8]=[CH2:9])[CH:5]=[CH:4][C:3]=1[F:10].[NH:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>COCCOC.C(Cl)Cl.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:10][C:3]1[CH:4]=[CH:5][C:6]([CH:8]=[CH2:9])=[CH:7][C:2]=1[N:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1

Participants

7

Reactant 3

HCID 8083MorpholineHCID 62657Potassium Phosphate, TribasicHCID 218646502-Bromo-4-ethenyl-1-fluorobenzene

Product 1

HCID 218646624-(2-Fluoro-5-vinyl-phenyl)-morpholine

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6344DichloromethaneSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 2-Bromo-1-fluoro-4-vinyl-benzene (8 g), morpholine (20 mL), Pd2(dba)3 (1.83 g), di-t-butyl-biphenylphosphine (1.2 g), K3PO4 (17 g) in DME (60 mL) was stirred at reflux for 4 h. The reaction mixture was cooled down to room temperature, diluted with methylene chloride, and filtered. The filtrate was concentrated in vacuo. The crude product was purified by Flash Chromatography of Biotage eluting with 7% ethyl acetate in hexanes to give the title compound as an oil (5 g).

Workup

  1. temperatureat reflux for 4 h
  2. filtrationfiltered
  3. concentrationThe filtrate was concentrated in vacuo
  4. customThe crude product was purified by Flash Chromatography of Biotage
  5. washeluting with 7% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-f61ac025c53b4deeaacb1812444d7bf4
Source dataset
uspto-grants-2006_05
Patent number
US07045551B2

Reaction notes

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