Sodium Acetate → 3,3,3-Trifluoro-2-oxopropanal 1-(4-bromo-2-fluoro-5-isopropoxyphenylhydrazone)

HRID 48490

Reaction equation

C([O-])(=O)C.[Na+].Br[CH:7](Br)[C:8]([C:10]([F:13])([F:12])[F:11])=[O:9].Cl.[Br:16][C:17]1[C:22]([O:23][CH:24]([CH3:26])[CH3:25])=[CH:21][C:20]([NH:27][NH2:28])=[C:19]([F:29])[CH:18]=1>O>[Br:16][C:17]1[C:22]([O:23][CH:24]([CH3:25])[CH3:26])=[CH:21][C:20]([NH:27][N:28]=[CH:7][C:8](=[O:9])[C:10]([F:13])([F:12])[F:11])=[C:19]([F:29])[CH:18]=1

Participants

Conditions

Temperature: 80 °C

Procedure

First, 50 g (0.61 mol) of sodium acetate and 41 g (0.14 mol) of 1,1-dibromo-3,3,3-trifluoroacetone were mixed with 500 ml of water, and the mixture was stirred at 80° C. for 30 minutes and then cooled to 0° C. Then, 45 g (0.14 mol) of 4-bromo-2-fluoro-5-isopropoxyphenylhydrazine hydrochloride was added at 10° C. or lower, and the mixture was stirred at 10° C. or lower for 3 hours. The precipitated crystals were collected by filtration and dried, which afforded 35 g (94.3 mmol) of 3,3,3-trifluoro-2-oxopropanal 1-(4-bromo-2-fluoro-5-isopropoxyphenylhydrazone).

Workup

temperaturecooled to 0° C
stirringlower, and the mixture was stirred at 10° C. or lower for 3 hours
filtrationThe precipitated crystals were collected by filtration
customdried

Sources & evidence

ORD record: ord-12e43ba8c0a54ca287305fcda8c0e43d
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06703503B2

Linked notes

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