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

HRID 1382661Notes

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]

Participants

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

stirringstirring
waitwas carried out for 10 minutes
customby decanting
washwashing with water
customdrying
customThe residue was chromatographed on silica
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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