Phosphate → 2-(3,4-Difluorophenyl)-2-methyloxirane

HRID 1275211Notes

Reaction equation

HRID 1275211 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:10])=[CH2:9])=[CH:4][C:3]=1[F:11].P([O-])([O-])([O-])=[O:13].ClC1C=C(C=CC=1)C(OO)=O>C(Cl)Cl>[F:11][C:3]1[CH:4]=[C:5]([C:8]2([CH3:10])[CH2:9][O:13]2)[CH:6]=[CH:7][C:2]=1[F:1]

Participants

5

Reactant 3

HCID 1061PhosphateHCID 70297m-Chloroperbenzoic acidHCID 155252121,2-Difluoro-4-(prop-1-en-2-yl)benzene

Product 1

HCID 229935082-(3,4-Difluorophenyl)-2-methyloxirane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a biphasic solution of 1,2-difluoro-4-isopropenyl-benzene (0.81 g, 5.1 mmol) in CH2Cl2 (50 mL) and 50 mL of phosphate buffer (made by dissolving 0.3 g of NaHPO4 and 0.35 g of NaH2PO4 in 50 mL water, pH=8) at 0° C., was added a solution of 3-chloroperoxybenzoic acid (approx. 75% solid, 3.32 g, 10.2 mmol) via a dropping funnel fitted with a cotton plug dropwise in two batches. The solution was stirred at room temperature overnight. It was extracted with CH2Cl2, washed with sat. Na2S2O4 solution followed by water. The organic layer was finally washed with sat. NaHCO3, separated, dried over Na2SO4, filtered and solvent was removed in vacuo. 2-(3,4-Difluorophenyl)-2-methyl-oxirane was obtained as a pale yellow oil (0.65 g, 74% yield). It was used in the next step without purification.

Workup

  1. customfitted with a cotton plug dropwise in two batches
  2. extractionIt was extracted with CH2Cl2
  3. washwashed with sat. Na2S2O4 solution
  4. washThe organic layer was finally washed with sat. NaHCO3
  5. customseparated
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customsolvent was removed in vacuo

Sources & evidence

ORD record
ord-854da8be63b4464a8b5507abbf4f34ae
Source dataset
uspto-grants-2000_12
Patent number
US06159990

Reaction notes

Loading…