Ethyl Acetate → HCID 59473785, compound

HRID 2069834Notes

Reaction equation

HRID 2069834 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:9]([CH3:11])[CH3:10])[CH:5]=[C:6]([CH3:8])[CH:7]=1.C([O-])(=O)C.[NH4+].[Br:17]N1C(=O)CCC1=O.CCOC(C)=O>C(#N)C>[Br:17][C:7]1[C:6]([CH3:8])=[CH:5][C:4]([N:9]([CH3:10])[CH3:11])=[CH:3][C:2]=1[F:1]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 517165Ammonium AcetateHCID 13782118HCID 13782118, compound

Product 1

HCID 59473785HCID 59473785, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of (3-Fluoro-5-methyl-phenyl)-dimethyl-amine (2.82 g, 18.4 mmol) in acetonitrile (28 mL) were sequentially added ammonium acetate (0.142 g, 1.84 mmol) and a solution of N-bromosuccinimide (3.27 g, 18.4 mmol) in acetonitrile (23 mL) drop-wise at 0° C. After 1 h., at r.t., the solvent was switched to EtOAc, and the solution was washed with saturated NaHCO3 (aq), dried (MgSO4), filtered, and concentrated in vacuo to give an orange, oily residue. Purification of this oil by flash chromatography (SiO2, 5% EtOAc/Hexanes) gave (4-Bromo-3-fluoro-5-methyl-phenyl)-dimethyl-amine as an ivory solid (3.96 g, 93%).

Workup

  1. customat 0° C
  2. customat r.t.
  3. washthe solution was washed with saturated NaHCO3 (aq)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give an orange, oily residue
  8. customPurification of this oil by flash chromatography (SiO2, 5% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-7e13c5a8051a434ea26ba792bef05999
Source dataset
uspto-grants-2012_10
Patent number
US08299077B2

Reaction notes

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