Dimethylformamide → HCID 22649666, compound

HRID 445372Notes

Reaction equation

HRID 445372 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[CH3:9][O:10][CH2:11][CH2:12]Br.C(=O)([O-])[O-].[Na+].[Na+].CN(C=O)C>O>[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][CH2:12][CH2:11][O:10][CH3:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 97314-FluoroanilineHCID 10340Sodium CarbonateHCID 809722-Bromoethyl methyl ether

Product 1

HCID 22649666HCID 22649666, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a 50 mL round-bottomed flask was added 4-fluoroaniline (383 μL, 3971 μmol, Aldrich), 2-bromoethyl methyl ether (552 μL, 3971 μmol, Aldrich), sodium carbonate (667 mg, 7943 μmol), DMF (2 mL). The reaction mixture was stirred at 80° C. for overnight (ca 17 h). The mixture was cooled down to RT. The reaction mixture was diluted with water (30 mL) and extracted with EtOAc (2×40 mL). The organic extract was washed with water (20 mL), saturated NaCl (20 mL), dried over Na2SO4, filtered and concentrated in vacuo and the residue was purified by silica gel chromatography, eluting with 30% EtOAc/hexanes to give 4-fluoro-N-(2-methoxyethyl)benzenamine. MS (ESI pos. ion) m/z: 170 (M+1).

Workup

  1. temperatureThe mixture was cooled down to RT
  2. extractionextracted with EtOAc (2×40 mL)
  3. extractionThe organic extract
  4. washwas washed with water (20 mL), saturated NaCl (20 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customthe residue was purified by silica gel chromatography
  9. washeluting with 30% EtOAc/hexanes

Sources & evidence

ORD record
ord-d9bac153140d4e27b5c133fcaa0dacd7
Source dataset
uspto-grants-2013_07
Patent number
US08476297B2

Reaction notes

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