Triethylamine → HCID 58909965, compound

HRID 1295948Notes

Reaction equation

HRID 1295948 reaction equation
C(N(CC)CC)C.[C:8]([C:12]1[CH:13]=[C:14]([C:23](=[O:25])[CH3:24])[CH:15]=[C:16]([N:20]([CH3:22])[CH3:21])[C:17]=1[O:18][CH3:19])([CH3:11])([CH3:10])[CH3:9].[Br:26]N1C(=O)CCC1=O.C(OCC)(=O)C>O1CCCC1>[Br:26][CH2:24][C:23]([C:14]1[CH:15]=[C:16]([N:20]([CH3:22])[CH3:21])[C:17]([O:18][CH3:19])=[C:12]([C:8]([CH3:11])([CH3:9])[CH3:10])[CH:13]=1)=[O:25]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 67184N-bromobutanimideHCID 589100481-[3-(tert-Butyl)-5-(dimethylamino)-4-methoxyphenyl]-1-ethanone

Product 1

HCID 58909965HCID 58909965, compoundYield 87.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (3.2 ml, 22.9 mmol) and tert-butyl dimethylsilyltrifluoromethanesulfonate (3.02 g, 11.4 mmol) were added to a solution of 1-[3-(tert-butyl)-5-(dimethylamino)-4-methoxyphenyl]-1-ethanone (1.9 g, 7.63 mmol) in tetrahydrofuran (50 ml) while cooling on ice and the mixture was stirred at the same temperature for 30 minutes, after which N-bromosuccinimide (2.7 g, 15.2 mmol) was added and stirring was continued for 30 minutes. Ethyl acetate was added, the reaction mixture was washed with brine and the organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and then the residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (2.2 g) as a white solid.

Workup

  1. temperaturewhile cooling on ice
  2. stirringstirring
  3. waitwas continued for 30 minutes
  4. washthe reaction mixture was washed with brine
  5. dry with materialthe organic layer was dried 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-f44c6e2377a94d4683ea4fee1cac7163
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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