Dimethylformamide → 3-[4-(Trifluoromethyl)phenyl]prop-2-enoyl chloride

HRID 1843893Notes

Reaction equation

CN(C=O)C.[F:6][C:7]([F:20])([F:19])[C:8]1[CH:13]=[CH:12][C:11]([CH:14]=[CH:15][C:16](O)=[O:17])=[CH:10][CH:9]=1.O=S(Cl)[Cl:23].C(OC(=O)C)C>C(Cl)Cl.CCCCCC>[F:6][C:7]([F:20])([F:19])[C:8]1[CH:13]=[CH:12][C:11]([CH:14]=[CH:15][C:16]([Cl:23])=[O:17])=[CH:10][CH:9]=1

Participants

Conditions

Temperature: 0 °C

Procedure

DMF (0.3 mL) was added to a solution of 3-(4-trifluoromethyl-phenyl)-acrylic acid (I-29a: 4 g, 0.018 mol) in DCM (30 mL). The reaction mixture was stirred at 0° C. under nitrogen atmosphere. This was followed by the addition of SOCl2 (2.62 g, 0.022 mol) and the resulting mixture was refluxed at 75° C. for 3 hours. The reaction was monitored by TLC (30% ethylacetate in hexane). The reaction mixture was cooled to room temperature and concentrated to afford the crude product which was dissolved in 1,4-dioxane and used in the next step without further purification.

Workup

temperaturethe resulting mixture was refluxed at 75° C. for 3 hours
temperatureThe reaction mixture was cooled to room temperature
concentrationconcentrated

Sources & evidence

ORD record: ord-dd7998db2b3b4cd3a14ed9323dc1b9f9
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946260B2

Reaction notes

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