Methanesulfonic Acid → 4-Chloro-2-fluoro-fluoren-9-one
Reaction equation
O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O.CS(O)(=O)=O.[Cl:20][C:21]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=1[C:28]1[C:29]([C:34]([OH:36])=O)=[CH:30][CH:31]=[CH:32][CH:33]=1>O>[Cl:20][C:21]1[C:22]2[C:28]3[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:34](=[O:36])[C:23]=2[CH:24]=[C:25]([F:27])[CH:26]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a mixture of phosphorus pentoxide (133 g) and methanesulfonic acid (1300 ml) was added 2′-chloro-4′-fluoro-biphenyl-2-carboxylic acid (132.9 g), and the mixture was stirred at 80° C. for 2.5 hr. The reaction mixture was ice-cooled, water (1300 ml) was slowly added dropwise, and the mixture was further stirred at room temperature for 1 hr. This suspension was filtered, and the obtained solid was washed with water (300 ml). The solid was mixed with 50 v/v % ethanol-water (1300 ml), and the slurry was stirred at room temperature for 1.5 hr, and filtered. The obtained solid was washed with 50 v/v % ethanol-water (200 ml), air-dried for 3 hr, and dried under reduced pressure at 60° C. to give the title compound (121.6 g, 99%).
Workup
- temperaturecooled
- stirringthe mixture was further stirred at room temperature for 1 hr
- filtrationThis suspension was filtered
- washthe obtained solid was washed with water (300 ml)
- additionThe solid was mixed with 50 v/v % ethanol-water (1300 ml)
- stirringthe slurry was stirred at room temperature for 1.5 hr
- filtrationfiltered
- washThe obtained solid was washed with 50 v/v % ethanol-water (200 ml)
- customair-dried for 3 hr
- customdried under reduced pressure at 60° C.
Sources & evidence
- ORD record
- ord-585b0401fa034d52ae518a1475c44725
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08343994B2
Reaction notes
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