Phosphorus Pentoxide-Methanesulfonic Acid → 4-Chloro-2-methoxy-9H-fluoren-9-one

HRID 579380Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]1[C:11]([C:16]([OH:18])=O)=[CH:12][CH:13]=[CH:14][CH:15]=1.CS(O)(=O)=O.O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>O>[Cl:1][C:2]1[C:3]2[C:10]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:16](=[O:18])[C:4]=2[CH:5]=[C:6]([O:8][CH3:9])[CH:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Under an argon atmosphere, to 2′-chloro-4′-methoxybiphenyl-2-carboxylic acid (65.4 g) was added an Eaton reagent (phosphorus pentoxide-methanesulfonic acid (weight ratio 1:10) solution, 330 ml), and the mixture was stirred at an oil bath temperature of 100° C. for 1 hr. The reaction mixture was ice-cooled, water (650 ml) was slowly added dropwise, and the mixture was stirred at room temperature for 1 hr. The precipitated solid was collected by filtration, and washed with water (500 ml). The obtained solid was air-dried overnight to give the title compound (92.0 g).

Workup

temperaturecooled
stirringthe mixture was stirred at room temperature for 1 hr
filtrationThe precipitated solid was collected by filtration
washwashed with water (500 ml)
customThe obtained solid was air-dried overnight

Sources & evidence

ORD record: ord-7e6dac76bd994fd3825e4e14e805db52
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09040717B2

Reaction notes

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