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Sodium Bicarbonate → 1-(3-Chloro-4-bromophenyl)-3-trifluoromethyl-4-fluoro-4-allyl-5-pyrazolone

HRID 1382661
Notes
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Reaction equation

HRID 1382661 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[C:12]([CH2:16][CH:17]=[CH2:18])(O)[C:11]([C:19]([F:22])([F:21])[F:20])=[N:10]2)[CH:5]=[CH:6][C:7]=1[Br:8].C(N(SN(CC)CC)CC)C.[F-:34].[F-].[F-].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[C:12]([F:34])([CH2:16][CH:17]=[CH2:18])[C:11]([C:19]([F:22])([F:21])[F:20])=[N:10]2)[CH:5]=[CH:6][C:7]=1[Br:8]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 212728871-(3-Chloro-4-bromophenyl)-3-trifluoromethyl-4-allyl-4-hydroxy-5-pyrazoloneHCID 86605672Diethylaminosulfide trifluoride

Product 1

HCID 212728901-(3-Chloro-4-bromophenyl)-3-trifluoromethyl-4-fluoro-4-allyl-5-pyrazolone

Reagents, catalysts & solvents 1

HCID 6344Dichloromethane
Solvent

Conditions

Temperature
-3 °C

Procedure

4 g of 1-(3-chloro-4-bromophenyl)-3-trifluoromethyl-4-allyl-4-hydroxy-5-pyrazolone in 200 ml of methylene chloride were cooled to -10° C. and 2.7 ml of trifluoride diethylaminosulfide were added all at once. The mixture was stirred for one hour at -10° C./-3° C. 120 ml of a saturated solution of sodium bicarbonate were added and stirring was carried out for 10 minutes, followed by decanting, washing with water, drying and bringing to dryness. The residue was chromatographed on silica and eluted with a hexane-methylene chloride mixture (8-2) to obtain 1.1 g of 1-(3-chloro-4-bromophenyl)-3-trifluoromethyl-4-fluoro-4-allyl-5-pyrazolone.

Workup

  1. stirringstirring
  2. waitwas carried out for 10 minutes
  3. customby decanting
  4. washwashing with water
  5. customdrying
  6. customThe residue was chromatographed on silica
  7. washeluted with a hexane-methylene chloride mixture (8-2)

Sources & evidence

ORD record
ord-212ae14063614531ad92884360c6a48f
Source dataset
uspto-grants-1989_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04808210

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes