Chloroform → HCID 178463143, compound

HRID 254208Notes

Reaction equation

HRID 254208 reaction equation
B(Br)(Br)Br.[Cl:5][CH2:6][C:7]1([CH3:27])[O:11][N:10]=[C:9]([S:12][CH2:13][C:14]2[C:15]([C:23]([F:26])([F:25])[F:24])=[N:16][N:17]([CH2:21][CH3:22])[C:18]=2[O:19]C)[CH2:8]1.C(Cl)(Cl)Cl>ClCCl>[Cl:5][CH2:6][C:7]1([CH3:27])[O:11][N:10]=[C:9]([S:12][CH2:13][C:14]2[C:15]([C:23]([F:26])([F:25])[F:24])=[N:16][N:17]([CH2:21][CH3:22])[C:18]=2[OH:19])[CH2:8]1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 25134Boron tribromideHCID 22934885HCID 22934885, compound

Product 1

HCID 178463143HCID 178463143, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10 ml of boron tribromide (2 M/liter of dichloromethane solution, 20.2 mmoles) was added, at −60° C., into a solution of 2.5 g (6.7 mmoles) of 5-chloromethyl-3-(1-ethyl-5-methoxy-3-trifluoromethyl-1H-pyrazol-4-ylmethylthio)-5-meth-yl-2-isoxazoline dissolved in 30 ml of dichloromethane. The mixture was stirred at room temperature overnight to give rise to a reaction. After the completion of the reaction, the reaction mixture was poured into ice water and extraction with chloroform was conducted. The resulting organic layer was washed with water and an aqueous sodium chloride solution in this order and then dried over anhydrous magnesium sulfate. The resulting solution was subjected to reduced pressure distillation to remove the solvent contained therein. The residue was purified by silica gel column chromatography to obtain 1.6 g (yield: 66.7%) of 5-chloromethyl-3-(1-ethyl-5-hydroxy-3-trifluoromethyl-1H-pyrazol-4-ylmethylthio)-5-methyl-2-isoxazoline.

Workup

  1. customto give rise
  2. customto a reaction
  3. customAfter the completion of the reaction
  4. washThe resulting organic layer was washed with water
  5. dry with materialan aqueous sodium chloride solution in this order and then dried over anhydrous magnesium sulfate
  6. distillationThe resulting solution was subjected to reduced pressure distillation
  7. customto remove the solvent
  8. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2572aa24a6624a3c8c2e01d446a2ae4f
Source dataset
uspto-grants-2011_01
Patent number
US07875606B2

Reaction notes

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