3-Bromophenylhydrazine hydrochloride → HCID 118431677, compound

HRID 2207915Notes

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:23]=[C:24]([NH:28][NH2:29])[CH:25]=[CH:26][CH:27]=1>C(O)(=O)C>[Br:21][C:22]1[CH:23]=[C:24]([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:25]=[CH:26][CH:27]=1

Participants

Conditions

Temperature: 95 °C

Procedure

1-(2,4-Difluoro-phenyl)-4,4,5,5,5-pentafluoro-pent-1-en-3-one (4.8 g, 16.9 mmol) prepared in Step 3 and 3-bromophenylhydrazine hydrochloride (4.2 g, 18.6 mmol) were added to acetic acid (50.0 mL). The reaction mixture was stirred at 95° C. for 5 hours, concentrated under reduced pressure, and then ethyl acetate was added thereto. The mixture was washed with a saturated solution of sodium hydrogen carbonate, 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: n-hexane) to give 2.7 g of the titled compound as a yellow liquid.

Workup

concentrationconcentrated under reduced pressure
additionethyl acetate was added
washThe mixture was washed with a saturated solution of sodium hydrogen carbonate
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: n-hexane)

Sources & evidence

ORD record: ord-c81bc1f93b47424cbb64eeaf0825993f
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09376420B2

Reaction notes

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