Ethyl Acetate → 7-fluoro-6-(trifluoromethyl)-2,3-dihydro-1H-inden-1-one

HRID 1844041Notes

Reaction equation

ClS(O)(=O)=O.[F:6][C:7]1[CH:8]=[C:9]([CH2:17][CH2:18][C:19]([OH:21])=O)[CH:10]=[CH:11][C:12]=1[C:13]([F:16])([F:15])[F:14].C(OCC)(=O)C>CCCCCC>[F:6][C:7]1[C:12]([C:13]([F:14])([F:15])[F:16])=[CH:11][CH:10]=[C:9]2[C:8]=1[C:19](=[O:21])[CH2:18][CH2:17]2

Participants

Conditions

Temperature: 0 °C

Procedure

Chlorosulfonic acid (12.6 mL) was added to a stirred solution of 3-(3-fluoro-4-(trifluoromethyl)phenyl)propanoic acid (I-77b: 1.0 g, 4.2707 mmol). The resulting mixture was stirred for 5 hours at 0° C. The reaction was monitored by TLC (20% ethyl acetate in hexane). The reaction mixture was quenched with ice water and extracted with chloroform (2×150 mL). The organic layer was dried over Na2SO4 and concentrated under reduced pressure to afford the crude product. Purification by column chromatography on silica gel (5% ethyl acetate in hexane), afforded 550 mg of the product (58.9% yield).

Workup

customThe reaction mixture was quenched with ice water
extractionextracted with chloroform (2×150 mL)
dry with materialThe organic layer was dried over Na2SO4
concentrationconcentrated under reduced pressure
customto afford the crude product
customPurification by column chromatography on silica gel (5% ethyl acetate in hexane)

Sources & evidence

ORD record: ord-efb267bb97ad4d568331775cd6c725be
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946260B2

Reaction notes

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