3-(3-Fluorophenyl)propionic acid → 5-Fluoro-1-indanone

HRID 1844046Notes

Reaction equation

HRID 1844046 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][C:10]([OH:12])=O)[CH:5]=[CH:6][CH:7]=1>ClS(O)(=O)=O>[F:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][CH:7]=1)[C:10](=[O:12])[CH2:9][CH2:8]2

Participants

3

Reactant 1

HCID 27374893-(3-Fluorophenyl)propionic acid

Product 1

HCID 1365375-Fluoro-1-indanoneYield 70.5%

Reagents, catalysts & solvents 1

HCID 24638Chlorosulfonic acidSolvent

Procedure

3-(3-Fluorophenyl)propanoic acid (I-78b: 2.0 gm, 11.8 mmol) was cyclized with chlorosulfonic acid (20 mL) to afford the crude product. Purification by column chromatography on silica gel (10% ethyl acetate in hexane), afforded 1.2 g of the product (70.5% yield).

Workup

  1. customto afford the crude product
  2. customPurification by column chromatography on silica gel (10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-2664b470a44b4859aa852740ccf35d7b
Source dataset
uspto-grants-2015_02
Patent number
US08946260B2

Reaction notes

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