Hydrochloric Acid → HCID 18424411, compound

HRID 1282415Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1I.[F:13][CH2:14][C:15]([CH2:19][F:20])([OH:18])[C:16]#[CH:17].C(N(CC)CC)C.Cl>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CCCCCC.C(OCC)(=O)C.CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[C:17]#[C:16][C:15]([CH2:19][F:20])([OH:18])[CH2:14][F:13]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 4-chloro-3-iodobenzotrifluoride (63.3 g), 1-fluoro-2-fluoromethyl-3-butyn-2-ol (28.8 g), triethylamine (26.2 g), cuprous iodide (0.38 g), bis(triphenylphosphine)palladium chloride (1.40 g) and N,N-dimethylformamide (100 ml) was stirred under a nitrogen atmosphere under heating at 80° C. for 1.5 hours. To the reaction mixture, 2 N HCl and a hexane/ethyl acetate mixed solvent (3/1) were added and the insoluble matter was filtered off with Celite; following extraction with a hexane/ethyl acetate mixed solvent (3/1), the resulting organic layers were combined, washed with a saturated aqueous solution of sodium chloride, dried with anhydrous sodium sulfate and concentrated under reduced pressure; the resulting residue was purified by distillation to give 4-(2-chloro-5-trifluoromethylphenyl)-1-fluoro-2-fluoromethyl-3-butyn-2-ol (44.5 g) having a boiling point of 105-107° C./1 mmHg.

Workup

filtrationthe insoluble matter was filtered off with Celite
extractionextraction with a hexane/ethyl acetate mixed solvent (3/1)
washwashed with a saturated aqueous solution of sodium chloride
dry with materialdried with anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
distillationthe resulting residue was purified by distillation

Sources & evidence

ORD record: ord-f2673340574a495e868696526bc42ce4
Source dataset: uspto-grants-2002_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06455708B1

Reaction notes

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