m-Chloroperbenzoic acid → HCID 53948112, compound

HRID 1419945Notes

Reaction equation

HRID 1419945 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH3:11])=[C:6]([F:12])[CH:5]=1)[CH:2]=[CH2:3].ClC1C=CC=C(C(OO)=[O:21])C=1>C(Cl)Cl>[F:12][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][C:7]=1[O:10][CH3:11])[CH2:1][CH:2]1[CH2:3][O:21]1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 27590044-allyl-2-fluoroanisole

Product 1

HCID 53948112HCID 53948112, compoundYield 37.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Allyl-2-fluoro-1-methoxy benzene (1.2 g, 7.22 mmol) was dissolved in CH2Cl2 (35 ml) and treated successively with buffer pH=7.95 (35 ml, NaH2PO4 --Na2HPO4) and m-chloroperbenzoic acid 70% (2.2 g, 9 mmol). Reaction mixture was stirred at room temperature for 63 hours. The aqueous phase was extracted with CH2Cl2 (4×30 ml), combined organic phases were washed with sat. NaHCO3 (50 ml), dried over Na2SO4 and concentrated. The residue was chromatographed over siliga gel (hexan-ethyl acetate 9:1) to provide (RS)-2-(3-Fluoro-4-methoxy-benzyl)-oxirane (0.49 g, 37%) as a yellow oil MS: m/e=182 (M+).

Workup

  1. customReaction mixture
  2. extractionThe aqueous phase was extracted with CH2Cl2 (4×30 ml)
  3. washwere washed with sat. NaHCO3 (50 ml)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was chromatographed over siliga gel (hexan-ethyl acetate 9:1)

Sources & evidence

ORD record
ord-84a62dc20abd4ba69c05f754ecdf3a9c
Source dataset
uspto-grants-1999_03
Patent number
US05889026

Reaction notes

Loading…