Hydrochloric Acid → Ethyl (2-fluoro-4-nitrophenyl)acetate
Reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH:11]([C:16]([O:18][CH3:19])=[O:17])C(OC)=O.O.[Cl-].[Li+].[Cl-].[Na+].Cl.[CH3:26]S(C)=O>C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[CH2:11][C:16]([O:18][CH2:19][CH3:26])=[O:17]Participants
Reactant 6
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
500 mg (1.84 mmol) of dimethyl (2-fluoro-4-nitrophenyl)malonate are dissolved in 10 ml of DMSO. 33.2 mg (1.84 mmol) of water and 313 mg (7.37 mmol) of lithium chloride are added, and the mixture is heated at 100° C. for 3 hours. The reaction solution is then poured into 30 ml of ethyl acetate and shaken with saturated sodium chloride solution and with dilute hydrochloric acid. The mixture is dried over sodium sulfate and the solvent is removed under reduced pressure. The oil obtained is purified by preparative HPLC. The product fractions are extracted with ethyl acetate. The combined organic phases are dried over sodium sulfate and the solvent is removed under reduced pressure. This gives an oil which, after seeding with product crystals, quickly crystallizes.
Workup
- dry with materialThe mixture is dried over sodium sulfate
- customthe solvent is removed under reduced pressure
- customThe oil obtained
- customis purified by preparative HPLC
- extractionThe product fractions are extracted with ethyl acetate
- dry with materialThe combined organic phases are dried over sodium sulfate
- customthe solvent is removed under reduced pressure
- customThis gives an oil which
- customquickly crystallizes
Sources & evidence
- ORD record
- ord-9e0ec4a134a94e80b6b2110756aabd4d
- Source dataset
- uspto-grants-2010_05
- Patent number
- US07723347B2
Reaction notes
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