Hydrochloric Acid → 5-(4-(difluoromethoxy)-2-hydroxy-3-methoxyphenyl)isobenzofuran-1(3H)-one

HRID 2171080Notes

Reaction equation

[F:1][CH:2]([F:26])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[C:15](=[O:19])[O:14][CH2:13]3)=[C:6]([O:20]COC)[C:5]=1[O:24][CH3:25].Cl>CO>[F:26][CH:2]([F:1])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[C:15](=[O:19])[O:14][CH2:13]3)=[C:6]([OH:20])[C:5]=1[O:24][CH3:25]

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirring solution of 5-(4-(difluoromethoxy)-3-methoxy-2-(methoxymethoxy)phenyl) isobenzofuran-1(3H)-one (1 g, 2.73 mmol) in methanol (75 mL) was added concentrated hydrochloride (5 mL) and the reaction mixture was heated to 50° C. for 1 h. The reaction mixture was cooled to RT and concentrated under reduced pressure. The obtained residue was basified with sodium bicarbonate solution and extracted with dichloromethane (3×). The combined dichloromethane layers were washed with brine, dried over sodium sulphate and concentrated under reduced pressure to afford the title compound as a solid (800 mg, 91%).

Workup

temperatureThe reaction mixture was cooled to RT
concentrationconcentrated under reduced pressure
extractionextracted with dichloromethane (3×)
washThe combined dichloromethane layers were washed with brine
dry with materialdried over sodium sulphate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-89c3afdcc2a144e2bbe266f33df7f240
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09051290B2

Reaction notes

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