m-Chloroperbenzoic acid → HCID 86727087, compound

HRID 2175873Notes

Reaction equation

HRID 2175873 reaction equation
[CH:1]([C:3]1[CH:10]=[CH:9][C:6]([C:7]#[N:8])=[C:5]([F:11])[C:4]=1[CH3:12])=[CH2:2].C1C=C(Cl)C=C(C(OO)=[O:21])C=1>C(Cl)Cl>[F:11][C:5]1[C:4]([CH3:12])=[C:3]([CH:1]2[CH2:2][O:21]2)[CH:10]=[CH:9][C:6]=1[C:7]#[N:8]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86727086HCID 86727086, compound

Product 1

HCID 86727087HCID 86727087, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-ethenyl-2-fluoro-3-methylbenzonitrile (4.60 g, 28.5 mmol) and mCPBA (85%, 12.3 g, 71.4 mmol) in 300 mL of DCM was stirred at room temperature for 120 hours. The reaction mixture was cooled to 0° C. and was washed subsequently with saturated NaHCO3 (50 mL), saturated Na2SO3 (50 mL), 5% NaOH (2×50 mL) and brine (50 mL), dried over anhydrous Na2SO4 and concentrated. The residue was purified by column chromatography (petrol ether:EtOAc=20:1) to afford the title compound: 1H-NMR (400 MHz, CDCl3) δ ppm 7.36-7.39 (m, 1H), 7.04-7.06 (m, 1H), 3.92-3.94 (m, 1H), 3.15-3.17 (m, 1H), 2.57-2.59 (m, 1H), 2.30 (d, J=2.0 Hz, 3H).

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. washwas washed subsequently with saturated NaHCO3 (50 mL), saturated Na2SO3 (50 mL), 5% NaOH (2×50 mL) and brine (50 mL)
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (petrol ether:EtOAc=20:1)

Sources & evidence

ORD record
ord-ad0a6aafd32b44e295c7d6b4139fe984
Source dataset
uspto-grants-2015_06
Patent number
US09062070B2

Reaction notes

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