Thionyl Chloride → HCID 118431732, compound

HRID 2207943Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=3[F:20])[N:11]=[C:10]([C:21]([OH:23])=O)[CH2:9]2)=[CH:4][CH:3]=1.S(Cl)([Cl:26])=O>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[N:12]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][C:14]=3[F:20])[N:11]=[C:10]([C:21]([Cl:26])=[O:23])[CH2:9]2)=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 118432180HCID 118432180, compound

Product 1

HCID 118431732HCID 118431732, compound

Conditions

Temperature: 100 °C

Procedure

5-(4-bromo-phenyl)-1-(2,4-difluoro-phenyl)-4,5-dihydro-1H-pyrazole-3-carboxylic acid (10.0 g, 26.2 mmol) prepared in Step 1 was added to thionyl chloride (100.0 mL). The reaction was stirred at 100° C. for 2 hours and then concentrated under reduced pressure. The resulting residue was concentrated under reduced pressure three times, along with using toluene, to give 5-(4-bromo-phenyl)-1-(2,4-difluoro-phenyl)-4,5-dihydro-1H-pyrazole-3-carbonyl chloride as a dark brown liquid.

Workup

concentrationconcentrated under reduced pressure
concentrationThe resulting residue was concentrated under reduced pressure three times, along with using toluene

Sources & evidence

ORD record: ord-bafc19e2c0e3489c970819125c4e6cef
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09376420B2

Reaction notes

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