Hydrochloric Acid → HCID 20231441, compound

HRID 2290558Notes

Reaction equation

HRID 2290558 reaction equation
Br[C:2]1[S:3][C:4]([C:7]2[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:8]=2[O:16][CH3:17])=[CH:5][CH:6]=1.[F:18][C:19]([F:24])([F:23])C([O-])=O.[Na+].Cl.C(Cl)Cl>CN(C)C(=O)C.[Cu]I>[CH3:17][O:16][C:8]1[CH:9]=[C:10]([N+:13]([O-:15])=[O:14])[CH:11]=[CH:12][C:7]=1[C:4]1[S:3][C:2]([C:19]([F:24])([F:23])[F:18])=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 517019Sodium TrifluoroacetateHCID 20231438HCID 20231438, compound

Product 1

HCID 20231441HCID 20231441, compoundYield 22.8%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 31374DimethylacetamideSolvent

Procedure

A stirred solution of 8.0 g (0.026 mole) of 2-bromo-5-(2-methoxy-4-nitrophenyl)thiophene, 13.9 g (0.1 mole) of sodium trifluoroacetate and 9.7 g (0.05 mole) of copper(I)iodide in 160 ml of dry N,N-dimethylacetamide was heated at 175° C. for four hours. The reaction mixture was cooled to room temperature then poured into 400 ml of 2N hydrochloric acid and ice (approximately 1:1). Methylene chloride was added and the resultant mixture filtered. The filtrate separated into two phases. The organic phase was separated then washed with three portions of 2N hydrochloric acid and one portion of water. The washed organic phase was dried over anhydrous sodium sulfate, filtered, and the filtrate evaporated to leave a residue. The residue was subjected to column chromatography on silica gel, eluting with toluene, to yield 1.8 g of a mixture of 2-(2-methoxy-4-nitrophenyl)-5-trifluoromethylthiophene and 2-(2-methoxy-4-nitrophenyl)thiophene.

Workup

  1. filtrationthe resultant mixture filtered
  2. customThe filtrate separated into two phases
  3. customThe organic phase was separated
  4. washthen washed with three portions of 2N hydrochloric acid and one portion of water
  5. dry with materialThe washed organic phase was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customthe filtrate evaporated
  8. customto leave a residue
  9. washeluting with toluene

Sources & evidence

ORD record
ord-111e0fa578724d79b31a80efad2f2105
Source dataset
uspto-grants-1986_10
Patent number
US04617316

Reaction notes

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