Phosphate → HCID 14645957, compound

HRID 2249006Notes

Reaction equation

HRID 2249006 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.[Ni](Br)Br>[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

6

Reactant 3

HCID 1061PhosphateHCID 82050Lithium BromideHCID 11287268HCID 11287268, compound

Product 1

HCID 14645957HCID 14645957, compoundYield 70.1%

Reagents, catalysts & solvents 2

HCID 278492Nickel(II) bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

To an ice-cooled solution of 1.05 g of (R)-(+)-2,3,4,5,6-pentafluorostyrene oxide in 10 ml of tetrahydrofuran, was added dropwise a solution of Li2NiBr4, which was prepared by adding 2.19 g of nickel (II) bromide to a suspension of 1.74 g of lithium bromide in 20 ml of tetrahydrofuran. After completion of addition, the solution was stirred for 15 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 1.02 g of (R)-(-)-2-bromo-1-(pentafluorophenyl)ethanol containing 15% of (+)-2-bromo-2-(pentafluorophenyl)ethanol.

Workup

  1. customwas prepared
  2. additionAfter completion of addition
  3. customThe resulted reaction mixture
  4. extractionwas extracted with ether
  5. extractionThe resultant extract
  6. dry with materialwas dried over magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-60c18f0946294ef48cf21ec118932877
Source dataset
uspto-grants-1991_08
Patent number
US05041641

Reaction notes

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