Chlorine → HCID 178478025, compound

HRID 259696Notes

Reaction equation

HRID 259696 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:12]=[CH:11][NH:10][N:9]=1.[Cl:13]Cl>C(O)(=O)C.C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:12]([Cl:13])=[CH:11][NH:10][N:9]=1

Participants

5

Reactant 2

HCID 24526ChlorineHCID 178478013HCID 178478013, compound

Product 1

HCID 178478025HCID 178478025, compoundYield 44.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 6344DichloromethaneSolvent

Procedure

6.8 g (0.038 mol ) of 3-(2'-chlorophenyl)-1H-pyrazole, prepared as in Example 9, are dissolved, at temperature and with stirring, in 30 ml of acetic acid. 2.9 g (0.0409 mol) of chlorine are then introduced into the reaction mixture. Stirring is maintained for 1 hour at room temperature and then the acetic acid is driven off under reduced pressure. The residue is taken up in methylene chloride and this organic solution is washed with an aqueous bicarbonate solution, then with water and then dried over Na2SO4 before being concentrated to dryness. The residue is chromatographed on a silica column (eluent: heptane/ethyl acetate 60/40). 3.6 g of 3-(2'-chlorophenyl)-4-chloro-1H-pyrazole (compound 96) are obtained, which is of honey-like consistency (yield 44%).

Workup

  1. dissolutionare dissolved, at temperature
  2. washthis organic solution is washed with an aqueous bicarbonate solution
  3. dry with materialwith water and then dried over Na2SO4
  4. concentrationbefore being concentrated to dryness
  5. customThe residue is chromatographed on a silica column (eluent: heptane/ethyl acetate 60/40)

Sources & evidence

ORD record
ord-4b64d2c37b0048bd8f517f798b07f32a
Source dataset
uspto-grants-1996_06
Patent number
US05523280

Reaction notes

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