Phosphate → HCID 14645957, compound
Reaction equation
[F:1][C:2]1[C:10]([F:11])=[C:9]([F:12])[C:8]([F:13])=[C:7]([F:14])[C:3]=1[C@H:4]1[O:6][CH2:5]1.[Br-:15].[Li+].P([O-])([O-])([O-])=O>O1CCCC1>[Br:15][CH2:5][C@@H:4]([C:3]1[C:2]([F:1])=[C:10]([F:11])[C:9]([F:12])=[C:8]([F:13])[C:7]=1[F:14])[OH:6]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To an ice-cooled solution of 10.51 g of (R)-(+)-2,3,4,5,6-pentafluorostyrene oxide in 100 ml of tetrahydrofuran, was added dropwise a solution of Li2CuBr4, which was prepared by adding 16.75 g of cupric bromide to a suspension of 13.03 g of lithium bromide suspended in 150 ml of tetrahydrofuran. After completion of addition, the solution was stirred for one hour in an ice bath, and for another two hours at room temperature. The resulted reaction mixture was poured into a 0.05 mol phosphate buffer, and was extracted with ether. The resultant extract was dried over magnesium sulfate, and the solvent was distilled off under reduced pressure, thereby obtaining 11.92 g of (R)-(-)-2-bromo-1-(pentafluorophenyl)ethanol containing 20% of (+)-2-bromo-2-(pentafluorophenyl)ethanol. This was subjected to isolation by silica gel column chromatography, thereby obtaining (R)-(-)-2-bromo-1-(pentafluorophenyl)ethanol and (+)-2-bromo-2-(pentafluorophenyl)ethanol respectively possessing the aforementioned physical properties.
Workup
- customwas prepared
- additionAfter completion of addition
- waitfor another two hours at room temperature
- customThe resulted reaction mixture
- extractionwas extracted with ether
- extractionThe resultant extract
- dry with materialwas dried over magnesium sulfate
- distillationthe solvent was distilled off under reduced pressure
Sources & evidence
- ORD record
- ord-fa5f4cd4597146868161327a72ede9a1
- Source dataset
- uspto-grants-1991_08
- Patent number
- US05041641
Reaction notes
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