Water → HCID 15457080, compound

HRID 1385946Notes

Reaction equation

[Cl:1][C:2]1[C:10]2[O:9][C:8]([CH2:11][O:12]C)=[CH:7][C:6]=2[C:5]([C:14]2[C:15](=[O:25])[N:16]([CH3:24])[C:17]([C:20]([F:23])([F:22])[F:21])=[CH:18][CH:19]=2)=[C:4]([F:26])[CH:3]=1.ClCCl.B(Br)(Br)Br.O>ClCCl>[Cl:1][C:2]1[C:10]2[O:9][C:8]([CH2:11][OH:12])=[CH:7][C:6]=2[C:5]([C:14]2[C:15](=[O:25])[N:16]([CH3:24])[C:17]([C:20]([F:22])([F:21])[F:23])=[CH:18][CH:19]=2)=[C:4]([F:26])[CH:3]=1

Participants

Conditions

Temperature: -65 °C

Procedure

0.20 g (0.51 mmol) of 3-(7-chloro-5-fluoro-2-methoxymethylbenzofuran-4-yl)-1-methyl-6-trifluoromethyl-2-(1H)-pyridone was dissolved in 10 ml of dichloromethane, and 1.54 ml (1.54 mmol) of a 1.0M boron tribromide dichloromethane solution was added thereto at ±65° C. The mixture was stirred at −65° C. for 1 hour and then poured into water, followed by stirring at room temperature for 30 minutes. Then, it was extracted with dichloromethane. After washing with water, the organic layer was dried over anhydrous magnesium sulfate. Dichloromethane was distilled off under reduced pressure. Then, the obtained crude crystals were washed with n-hexane to obtain 0.19 g (yield: 99%) of the desired product. Melting point: 145-147° C. 1H-NMR (300 MHz, CDCl3) δ value: 3.73(3H,s), 4.55(2H,s), 6.66(1H,s), 6.80(1H,d), 7.20(1H,d), 7.55(1H,d)ppm.

Workup

customat ±65° C
stirringby stirring at room temperature for 30 minutes
extractionThen, it was extracted with dichloromethane
washAfter washing with water
dry with materialthe organic layer was dried over anhydrous magnesium sulfate
distillationDichloromethane was distilled off under reduced pressure
customThen, the obtained crude crystals
washwere washed with n-hexane

Sources & evidence

ORD record: ord-860ef798557d490abfc882454cefcf3f
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06265349B1

Reaction notes

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