Methanesulfonic Acid → 4-Chloro-2-methyl-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]([CH3:27])[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]([CH3:27])[CH:26]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
To a mixture of phosphorus pentoxide (150 g) and methanesulfonic acid (1500 ml) was added 2′-chloro-4′-methyl-biphenyl-2-carboxylic acid (153 g), and the mixture was stirred at 80° C. for 2 hr. The reaction mixture was cooled to 0° C. While keeping the temperature of the reaction mixture at 90° C. or below, water (1500 ml) was added dropwise, and the mixture was further stirred at room temperature for 2 hr. This suspension was filtered, and the obtained solid was washed with water (1000 ml). The solid was suspended in 50 v/v % ethanol-water (1500 ml), and the slurry was stirred at room temperature for 2 hr, and filtered. The obtained solid was air-dried for 1 hr and dried under reduced pressure at 80° C. to give the title compound (140.12 g, 99%).
Workup
- temperatureThe reaction mixture was cooled to 0° C
- customat 90° C. or below
- stirringthe mixture was further stirred at room temperature for 2 hr
- filtrationThis suspension was filtered
- washthe obtained solid was washed with water (1000 ml)
- stirringthe slurry was stirred at room temperature for 2 hr
- filtrationfiltered
- customThe obtained solid was air-dried for 1 hr
- customdried under reduced pressure at 80° C.
Sources & evidence
- ORD record
- ord-386b08434b9f4f2083b2cc0bddaa1e6d
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08871934B2
Reaction notes
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