Dimethylformamide → HCID 84015811, compound

HRID 1477618Notes

Reaction equation

HRID 1477618 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]([F:13])([F:12])[F:11])=[CH:7][C:6]=2[CH:14]=1.C([Li])CCC.CN(C)[CH:22]=[O:23].[Cl-].[NH4+]>C(OCC)(=O)C.O1CCCC1>[F:11][C:10]([F:13])([F:12])[C:8]1[O:9][C:5]2[CH:4]=[CH:3][C:2]([CH:22]=[O:23])=[CH:14][C:6]=2[CH:7]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 252094245-Bromo-2-(trifluoromethyl)benzofuranHCID 178418339Butyllithium

Product 1

HCID 84015811HCID 84015811, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a tetrahydrofuran solution (12 mL) of 5-bromo-2(trifluoromethyl)benzofuran (587 mg, 2.21 mmol), n-butyl lithium (hexane solution, 1.59 mol/L) (1.70 mL, 2.66 mmol) was added at −78° C. and the resultant solution was stirred for 40 minutes. To the reaction solution, N,N-dimethylformamide (257 μL, 3.32 mmol) was added and the resultant mixture was stirred for 3 hours while the temperature of the mixture was raised to room temperature. After completion of the reaction, saturated ammonium chloride aqueous solution was added to the reaction solution and extraction with ethyl acetate from the resultant mixture was performed. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate) to obtain the title compound (180 mg, yield 39%).

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-9c97458f52bc483cba8faa88e04c7fa1
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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