Water → 2,2-Dichloro-3,3,3-trifluoro-1-(2,6-dichloro-4-nitrophenyl)-1-propanol

HRID 1073366Notes

Reaction equation

HRID 1073366 reaction equation
[Cl:1][C:2]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[C:6]([Cl:13])[C:3]=1[CH:4]=[O:5].[C:14]([C:18]([Zn]Cl)([Cl:20])[Cl:19])([F:17])([F:16])[F:15].C(C(Cl)(Cl)Cl)(F)(F)F.O>CN(C=O)C.C1COCC1.[Zn]>[Cl:19][C:18]([Cl:20])([C:14]([F:17])([F:16])[F:15])[CH:4]([C:3]1[C:2]([Cl:1])=[CH:9][C:8]([N+:10]([O-:12])=[O:11])=[CH:7][C:6]=1[Cl:13])[OH:5]

Participants

8

Reactant 4

HCID 962WaterHCID 96351,1,1-Trichloro-2,2,2-trifluoroethaneHCID 218388352,6-Dichloro-4-nitrobenzaldehydeHCID 178506323HCID 178506323, compound

Product 1

HCID 148485192,2-Dichloro-3,3,3-trifluoro-1-(2,6-dichloro-4-nitrophenyl)-1-propanol

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

3 g of 2,6-dichloro-4-nitro benzaldehyde were reacted, in 20 ml of anhydrous DMF under a nitrogen atmosphere, with CF3CCl2ZnCl prepared from 5 g of CF3CCl3 and 2.2 g of Zn in 10 ml of THF at 60° C. for 1 hour. The mixture was heated at 50° C. for 2 hours and at the end of the reaction it was poured into acidulated water and extracted repeatedly with ethyl ether.

Workup

  1. additionwas poured
  2. extractionextracted repeatedly with ethyl ether

Sources & evidence

ORD record
ord-74c3d48a7dcf426eb8066870b97680eb
Source dataset
uspto-grants-1990_11
Patent number
US04968847

Reaction notes

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