4-Fluorophenol → Toluene

HRID 258024Notes

Reaction equation

HRID 258024 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Cl[CH2:10][CH2:11][C:12](Cl)=[O:13]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]2[C:3]=1[CH2:10][CH2:11][C:12]2=[O:13].[C:2]1([CH3:10])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 97324-FluorophenolHCID 693643-Chloropropionyl chloride

Product 2

HCID 1140TolueneYield 86.1%HCID 152684884-Fluoro-7-hydroxy-2,3-dihydro-1H-inden-1-one

Procedure

4-Fluoro-7-hydroxy-indan-1-one is prepared in analogy to the non-fluorinated compound by the process of S. Wagatsuma et al. [Org. Prep. Proced. Int., 5(2), 1973, 65-70] in two steps: 1. esterification of 4-fluorophenol and 3-chloropropionyl chloride by refluxing both components in toluene (yield: 86.1%, b.p: 150° C./30 mm); 2. heating the ester in the presence of AlCl3 (yield: 53.9%, m.p.: 87° C.).

Sources & evidence

ORD record
ord-67f055399c3b45808e10e7359f97f5b8
Source dataset
uspto-grants-1993_11
Patent number
US05264458

Reaction notes

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