Water → N-[5-Bromo-3-(1-fluoro-1-methylethyl)-2-methoxyphenyl]-N,N-dimethylamine

HRID 1295969Notes

Reaction equation

HRID 1295969 reaction equation
C(N(S(F)(F)[F:7])CC)C.[Br:10][C:11]1[CH:12]=[C:13]([N:23]([CH3:25])[CH3:24])[C:14]([O:21][CH3:22])=[C:15]([C:17](O)([CH3:19])[CH3:18])[CH:16]=1.O>C(Cl)Cl>[Br:10][C:11]1[CH:16]=[C:15]([C:17]([F:7])([CH3:19])[CH3:18])[C:14]([O:21][CH3:22])=[C:13]([N:23]([CH3:25])[CH3:24])[CH:12]=1

Participants

5

Reactant 3

HCID 962WaterHCID 123472(Diethylamino)sulfur trifluorideHCID 589100492-[5-Bromo-3-(dimethylamino)-2-methoxyphenyl]-2-propanol

Product 1

HCID 58910057N-[5-Bromo-3-(1-fluoro-1-methylethyl)-2-methoxyphenyl]-N,N-dimethylamineYield 67.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Diethylaminosulfur trifluoride (620 mg) was added to a solution of 2-[5-bromo-3-(dimethylamino)-2-methoxyphenyl]-2-propanol (1 g) in methylene chloride while stirring on ice. After stirring for an additional 30 minutes while cooling on ice, water was added, extraction was performed with ethyl acetate, and the organic layer was washed with brine and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (680 mg) as an oil.

Workup

  1. stirringAfter stirring for an additional 30 minutes
  2. additionwas added
  3. extractionextraction
  4. washthe organic layer was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-9f16943a7f884981864baaab28f08279
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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