Methanesulfonic Acid → 6-Fluoro-5-methoxy-2,3-dihydro-1H-inden-1-one

HRID 2100724Notes

Reaction equation

HRID 2100724 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([OH:12])=O)=[CH:4][C:3]=1[O:13][CH3:14].CS(O)(=O)=O.[OH-].[Na+]>>[F:1][C:2]1[CH:7]=[C:6]2[C:5]([CH2:8][CH2:9][C:10]2=[O:12])=[CH:4][C:3]=1[O:13][CH3:14]

Participants

4

Reactant 3

HCID 6395Methanesulfonic AcidHCID 14798Sodium HydroxideHCID 210986063-(4-Fluoro-3-methoxyphenyl)propanoic acid

Product 1

HCID 552971586-Fluoro-5-methoxy-2,3-dihydro-1H-inden-1-oneYield 94.4%

Conditions

Temperature
90 °C

Procedure

3-(4-Fluoro-3-methoxy-phenyl)-propionic acid (2 g, 10 mmol) and Methanesulfonic acid (15 ml) were sealed in process vial (20 ml) and it was heated at 90° C. for 10 minutes under microwave irradiation. The mixture was poured into ice and neutralized with NaOH. The solid was collected and dried to give 1.7 g of product (93.5% yield). LC-MS: m/e 181 (MH+)

Workup

  1. customThe solid was collected
  2. customdried

Sources & evidence

ORD record
ord-4f1278597ec34af39fb5963e582eb545
Source dataset
uspto-grants-2009_08
Patent number
US07572809B2

Reaction notes

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