m-Chloroperbenzoic acid → 2-[(4-Nitrophenyl)methyl]oxirane

HRID 269983

Reaction equation

HRID 269983 reaction equation
ClC1C=C(C=CC=1)C(OO)=[O:6].[CH2:12]([C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1)[CH:13]=[CH2:14]>ClCCl>[N+:21]([C:18]1[CH:19]=[CH:20][C:15]([CH2:12][CH:13]2[CH2:14][O:6]2)=[CH:16][CH:17]=1)([O-:23])=[O:22]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 595953p-Allylnitrobenzene

Product 1

HCID 151819382-[(4-Nitrophenyl)methyl]oxiraneYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Add allyl tri-n-butylstannane (30.10 mmol, 9.33 ml) dropwise to a stirred solution of 4-iodo-nitrobenzene (5 g, 20.07 mmol), tetrakis-(triphenylphosphine) palladium(0) (1.16 g, 1 mmol) and copper (I) iodide (306 mg, 1.6 mmol) in 50 ml of dry 1,4-dioxane under argon atmosphere. Reflux the mixture for 24 hours and then cool to room temperature. Dilute the solution with 40 ml of diethyl ether and add 20 ml of saturated solution of KF and stir for 2 hours. Filter the mixture and wash the organic layer with water (20 ml), brine (20 ml) and dry over sodium sulfate. Evaporate the solution under reduced pressure and purify the residue by flash chromatography on silica gel using hexane-ethyl acetate as eluent (20:1) to afford 1.80 g (55%) of 1-allyl-4-nitrobenzene. Add a solution of 3-chloro-peroxybenzoic acid (5.98 g, 24.28 mmol), in 20 ml of dichloromethane to a solution of 1-allyl-4-nitro-benzene (1.8 g, 11.04 mmol) in 50 ml of dichloromethane and stir the mixture at room temperature overnight. Quench with saturated NaHCO3 (15 ml), and wash the organic layer three times with saturated NaHCO3 and dry over magnesium sulfate. Evaporate under reduced pressure to afford 1.4 g (71%) of the title compound.

Workup

  1. customQuench with saturated NaHCO3 (15 ml)
  2. washwash the organic layer three times with saturated NaHCO3
  3. dry with materialdry over magnesium sulfate
  4. customEvaporate under reduced pressure

Sources & evidence

ORD record
ord-b1162c66d6c44e2490c9b78fe36be217
Source dataset
uspto-grants-2008_11
Patent number
US07449477B2

Linked notes

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