2-bromo-3,5-difluoro-7-methoxy-9H-xanthen-9-one → 2-bromo-3,5-difluoro-7-methoxy-9-methyl-9H-xanthen-9-ol

HRID 335910

Reaction equation

[Br:1][C:2]1[C:15]([F:16])=[CH:14][C:13]2[O:12][C:11]3[C:6](=[CH:7][C:8]([O:18][CH3:19])=[CH:9][C:10]=3[F:17])[C:5](=[O:20])[C:4]=2[CH:3]=1.[CH3:21][Mg]Cl>C1COCC1>[Br:1][C:2]1[C:15]([F:16])=[CH:14][C:13]2[O:12][C:11]3[C:6](=[CH:7][C:8]([O:18][CH3:19])=[CH:9][C:10]=3[F:17])[C:5]([CH3:21])([OH:20])[C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 2-bromo-3,5-difluoro-7-methoxy-9H-xanthen-9-one (40 g, 117 mmol) and THF (300 mL) was cooled to 0° C. and treated with methylmagnesium chloride (58.6 mL, 176 mmol) (3M in THF). After stirring at this temperature for 20 minutes, the reaction was quenched by the addition of sataturated NH4Cl (500 mL). Brine was added and the mixture was extracted with EtOAc (3×100 mL). The combined organic extracts were dried with sodium sulfate, filtered and concentrated in vacuo to afford crude 2-bromo-3,5-difluoro-7-methoxy-9-methyl-9H-xanthen-9-ol as a brown solid that was carried on without further purification. MS m/z=339.0 [M+1−H2O].

Workup

customthe reaction was quenched by the addition of sataturated NH4Cl (500 mL)
additionBrine was added
extractionthe mixture was extracted with EtOAc (3×100 mL)
dry with materialThe combined organic extracts were dried with sodium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-6d31548d0ce94dba926180b1dce661c8
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883782B2

Linked notes

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