Reaction equation
[F:1][C:2]1[CH:3]=[C:4](Br)[CH:5]=[CH:6][C:7]=1[C:8]([F:14])([F:13])[C:9]([F:12])([F:11])[F:10].C([Mg]Cl)(C)C.[C:21](=[O:23])=[O:22].O>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[C:8]([F:14])([F:13])[C:9]([F:12])([F:11])[F:10])[C:21]([OH:23])=[O:22]Participants
Conditions
- Temperature
- -10 °C
Procedure
A solution of 16.0 g (99% by weight; 54.1 mmol) of 3-fluoro-4-(pentafluoroethyl)-bromobenzene in 110 ml of tetrahydrofuran was cooled to −10° C. Added dropwise over the course of 30 minutes were 36.8 ml of a 2M (73.6 mmol) solution of isopropylmagnesium chloride. The mixture was stirred at −10° C. for 2.5 hours and then cautiously poured onto an excess of dry ice. Then, 130 ml of water were added, and the mixture was subsequently extracted once with 10 ml of diethyl ether. The aqueous phase was acidified with half-concentrated hydrochloric acid and then extracted with four times 150 ml of diethyl ether. The combined organic phases were dried and the filtrate was freed from the solvent. The residue was recrystallized from chloroform, giving 10.7 g of product with a purity of 98% by weight.
Workup
- additionAdded dropwise over the course of 30 minutes
- extractionthe mixture was subsequently extracted once with 10 ml of diethyl ether
- extractionextracted with four times 150 ml of diethyl ether
- customThe combined organic phases were dried
- customThe residue was recrystallized from chloroform
Sources & evidence
- ORD record
- ord-91da815e66bd4776a8207ac8993ab984
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08603947B2
Linked notes
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