Chloroform → HCID 18536748, compound

HRID 412078

Reaction equation

HRID 412078 reaction equation
CC(C)([O-])C.[K+].[F:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:9]=1[C:17]([F:20])([F:19])[F:18].[CH:21](Cl)([Cl:23])[Cl:22].C(O)(=O)C.CO>O1CCCC1.[Cl-].[Na+].O.CCCCCC.C(OCC)(=O)C>[Cl:22][CH:21]([Cl:23])[C:12]1[C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:9]([C:17]([F:18])([F:19])[F:20])=[C:8]([F:7])[CH:13]=1

Participants

9

Reactant 4

HCID 6212ChloroformHCID 949542-Fluoro-5-nitrobenzotrifluorideHCID 10129899Acetic acid methanolHCID 23665647Potassium tert-butoxide

Product 1

HCID 18536748HCID 18536748, compoundYield 51.2%

Reagents, catalysts & solvents 4

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of potassium t-butoxide (1.25 g, 11.1 mmol) in tetrahydrofuran (25 ml) was slowly added dropwise a solution of 2-fluoro-5-nitrobenzotrifluoride (1.00 g, 4.78 mmol) and chloroform (599 mg, 5.02 mmol) in tetrahydrofuran (2.5 ml) at −78° C. After stirring for 15 minutes at the same temperature, acetic acid-methanol (1:1, 5 ml) was added and the temperature was raised to room temperature. Ethyl acetate and saturated brine were added to the reaction mixture, which was extracted with ethyl acetate. After washed with brine, the organic layer was dried over anhydrous magnesium sulfate and solvent was distilled off. The residue obtained was submitted to silica gel column chromatography [hexane→hexane-ethyl acetate(300:1)] to obtain 714 mg of title compound as pale yellow liquid. Yield 51%.

Workup

  1. additionwas added
  2. extractionwas extracted with ethyl acetate
  3. washAfter washed with brine
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate and solvent
  5. distillationwas distilled off
  6. customThe residue obtained

Sources & evidence

ORD record
ord-709a237c3984425b80c000aa069b163e
Source dataset
uspto-grants-2003_05
Patent number
US06562839B1

Linked notes

Loading…