Sodium Carbonate → 1-Bromo-2-dimethylamino-5-(trifluoromethoxy)benzene

HRID 1420844Notes

Reaction equation

HRID 1420844 reaction equation
[Br:1]Br.[CH3:3][N:4]([CH3:16])[C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]([F:15])([F:14])[F:13])=[CH:7][CH:6]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)(Cl)Cl.O>[CH3:3][N:4]([CH3:16])[C:5]1[CH:10]=[CH:9][C:8]([O:11][C:12]([F:13])([F:14])[F:15])=[CH:7][C:6]=1[Br:1]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 24408BromineHCID 187825851-Dimethylamino-4-(trifluoromethoxy)benzene

Product 1

HCID 187825371-Bromo-2-dimethylamino-5-(trifluoromethoxy)benzene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

Bromine (0.15 ml) was added dropwise to a stirred, cooled (0° C.) mixture of 1-dimethylamino-4-(trifluoromethoxy)benzene (Description 77, 600 mg) and sodium carbonate (620 mg) in chloroform (15 ml). The mixture was stirred for 1 h. and diluted with water. The organic layer was washed with brine, dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by chromatography on silica gel, eluting with hexane/EtOAc (99:1 increasing to 95:5) to give the title compound as an oil (300 mg). 1H NMR (360 MHz, CDCl3) δ2.79 (6 H, s), 7.06 (1 H, d, J 9 Hz), 7.14 (1 H, dd, J 6, 1.5 Hz), and 7.44 (1 H, d, J 2.0 Hz). m/z (ES+) m/z 270, 272 (M+1).

Workup

  1. temperaturecooled
  2. washThe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by chromatography on silica gel
  6. washeluting with hexane/EtOAc (99:1 increasing to 95:5)

Sources & evidence

ORD record
ord-88e6071b9212471790921265f7be6fbe
Source dataset
uspto-grants-2000_06
Patent number
US06071927

Reaction notes

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