Acetic Acid → HCID 118431647, compound

HRID 2207916Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH:9]=[CH:10][C:11](=O)[C:12]([F:18])([F:17])[C:13]([F:16])([F:15])[F:14].Cl.[Br:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][NH2:29])=[CH:24][CH:23]=1.C(O)(=O)C.Cl>C(O)C>[Br:21][C:22]1[CH:27]=[CH:26][C:25]([N:28]2[CH:9]([C:3]3[CH:4]=[CH:5][C:6]([F:8])=[CH:7][C:2]=3[F:1])[CH2:10][C:11]([C:12]([F:18])([F:17])[C:13]([F:16])([F:15])[F:14])=[N:29]2)=[CH:24][CH:23]=1

Participants

Conditions

Temperature: 100 °C

Procedure

1-(2,4-Difluoro-phenyl)-4,4,5,5,5-pentafluoro-pent-1-en-3-one (3.8 g, 13.3 mmol) prepared in Step 3 of Preparation 14, 4-bromophenylhydrazine hydrochloride (3.3 g, 13.5 mmol), acetic acid (15.0 mL) and conc. hydrochloric acid (20.0 mL) were added to ethanol (35.0 mL). The reaction mixture was stirred at 100° C. for 18 hours, quenched with a saturated solution of sodium hydrogen carbonate, and then extracted with ethyl acetate three times. The combined extract was washed with brine, dried on anhydrous magnesium sulfate, and then concentrated under reduced pressure to give a yellow liquid residue. The resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/10) to give 5.4 g of the titled compound as a yellow liquid.

Workup

customquenched with a saturated solution of sodium hydrogen carbonate
extractionextracted with ethyl acetate three times
extractionThe combined extract
washwas washed with brine
dry with materialdried on anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customto give a yellow liquid residue
customThe resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/10)

Sources & evidence

ORD record: ord-f08b8da824824ba7b50c8c5248920b40
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09376420B2

Reaction notes

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