Dimethylformamide → HCID 59803805, compound

HRID 253445Notes

Reaction equation

HRID 253445 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[O:9][CH2:10][C:11]([F:14])([F:13])[F:12].C([Li])CCC.CN(C)[CH:22]=[O:23]>O>[Cl:1][C:2]1[C:3]([O:9][CH2:10][C:11]([F:12])([F:13])[F:14])=[CH:4][CH:5]=[C:6]([F:8])[C:7]=1[CH:22]=[O:23]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 59803830HCID 59803830, compoundHCID 178418339Butyllithium

Product 1

HCID 59803805HCID 59803805, compoundYield 19.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 2-chloro-4-fluoro-1-(2,2,2-trifluoro-ethoxy)-benzene (124, 2.10 g, 9.19 mmol), under an atmosphere of nitrogen at −78° C., n-butyllithium (2.50 M in hexane, 3.86 mL) was added slowly. After 60 minutes, N,N-dimethylformamide (0.782 mL, 0.0101 mol) was added to the reaction. After 30 minutes, the reaction was allowed to warm to room temperature for 10 minutes. The reaction was poured into water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated and purified by silica gel column chromatography eluting with 20% ethyl acetate in hexane to give the desired compound (125, 450 mg, 19.0%).

Workup

  1. waitAfter 30 minutes
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated
  6. custompurified by silica gel column chromatography
  7. washeluting with 20% ethyl acetate in hexane

Sources & evidence

ORD record
ord-573aafc018b64b28a33024a90e9fb688
Source dataset
uspto-grants-2011_01
Patent number
US07872018B2

Reaction notes

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