Hydrochloric Acid → HCID 19971591, compound

HRID 1762644Notes

Reaction equation

HRID 1762644 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[O:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[F:17][C:18](I)([F:20])[F:19].Cl>CN(C)C=O.[Zn]>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]([OH:7])[C:18]([F:20])([F:19])[F:17])=[CH:4][C:3]=1[O:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 16843TrifluoroiodomethaneHCID 1100684-Fluoro-3-phenoxybenzaldehyde

Product 1

HCID 19971591HCID 19971591, compoundYield 56.7%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2 g of 4-fluoro-3-phenoxy-benzaldehyde, 5 ml of dimethylforomamide, 2 g of electrolytic zinc and 15 ml of a solution of 13.5 mmols of trifluoromethyl iodide in dimethylformamide was ultrasonically irradiated for 15 minutes and the mixture was poured into aqueous N hydrochloric acid. The mixture was extracted with isopropyl ether and the organic phase was evaporated to dryness under reduced pressure. The residue was chromatographed over silica gel and was eluted with a 1-1 methylene chloride-hexane mixture to be obtain 1.5 g of 1-(4-fluoro-3-phenoxy-phenyl)-2,2,2-trifluoroethanol.

Workup

  1. customwas ultrasonically irradiated for 15 minutes
  2. extractionThe mixture was extracted with isopropyl ether
  3. customthe organic phase was evaporated to dryness under reduced pressure
  4. customThe residue was chromatographed over silica gel
  5. washwas eluted with a 1-1 methylene chloride-hexane mixture

Sources & evidence

ORD record
ord-c0c718e5affb474680fc898cff5e46ea
Source dataset
uspto-grants-1989_05
Patent number
US04833163

Reaction notes

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