2-Bromopropane → Benzenamine, 4-fluoro-N-(1-methylethyl)-

HRID 717663Notes

Reaction equation

HRID 717663 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.Br[CH:10]([CH3:12])[CH3:11].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][CH:10]([CH3:12])[CH3:11])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 63582-BromopropaneHCID 97314-FluoroanilineHCID 11430Potassium Carbonate

Product 1

HCID 154403Benzenamine, 4-fluoro-N-(1-methylethyl)-Yield 43%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-fluoro-aniline (1.12 g; 10 mmol), 2-bromopropane (1.13 ml) and K2CO3 (1.38 g, 10 mmol) in anhydrous DMF (6 ml) was stirred for 5 h at reflux. The mixture was cooled to room temperature, diluted to 100 ml with H2O and extracted with EtOAc (50 ml). The organic layer was washed with H2O (2×20 ml) and dried over MgSO4 and filtered. The filtrate was evaporated to dryness and the residue was purified by FCC(SiO2, hexane/EtOAc) to give the title compound (0.65 g; 43%), as light yellow oil. 1H-NMR (CDCl3) 6.89-6.82 (m, 2H); 6.53-6.47 (m, 2H); 3.58-3.49 (m, 1H); 1.18 (d, 6H, J=6.25 Hz).

Workup

  1. temperatureat reflux
  2. extractionextracted with EtOAc (50 ml)
  3. washThe organic layer was washed with H2O (2×20 ml)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness
  7. customthe residue was purified by FCC(SiO2, hexane/EtOAc)

Sources & evidence

ORD record
ord-abf7c84cd7c9405e9338ff8e1a6930a1
Source dataset
uspto-grants-2015_11
Patent number
US09193716B2

Reaction notes

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