Carbon Dioxide → 2-Fluorobiphenyl-4-carboxylic Acid
Reaction equation
II.[Mg].Br[C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[C:7]([F:17])[CH:6]=1.[C:18](=[O:20])=[O:19].Cl>O1CCCC1>[F:17][C:7]1[CH:6]=[C:5]([C:18]([OH:20])=[O:19])[CH:10]=[CH:9][C:8]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 65 °C
Procedure
Few crystals of iodine are added to tetrahydrofuran (1400 mL) containing magnesium turnings (25.17 g, 1.035 mol). The mixture is heated at 60-70° C. A solution of 4-bromo-2-fluorobiphenyl (200 g, 0.797 mol) in tetrahydrofuran (600 mL) is added dropwise to the reaction mixture and refluxed for 1 hr. Reaction mixture is brought to room temperature and then cooled to −20° C. Carbon dioxide gas is passed through the reaction mixture for 45 minutes. The reaction mixture is treated with 3N HCl (500 mL) and extracted with ethyl acetate (2×500 mL). Combined organic layer is dried over sodium sulphate. Removal of solvent under reduced pressure gives a solid which is washed with diethyl ether (2×200 mL) and then dried to furnish 2-fluorobiphenyl-4-carboxylic acid.
Workup
- temperaturerefluxed for 1 hr
- customReaction mixture
- customis brought to room temperature
- temperaturecooled to −20° C
- extractionextracted with ethyl acetate (2×500 mL)
- dry with materialCombined organic layer is dried over sodium sulphate
- customRemoval of solvent under reduced pressure
- customgives a solid which
- washis washed with diethyl ether (2×200 mL)
- customdried
Sources & evidence
- ORD record
- ord-b63b7e32392242818b81b10530319c42
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08809539B2
Reaction notes
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