m-Chloroperbenzoic acid → HCID 86727089, compound

HRID 2175881Notes

Reaction equation

HRID 2175881 reaction equation
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[F:12][C:13]1[C:20]([O:21][CH3:22])=[C:19]([CH:23]=[CH2:24])[CH:18]=[CH:17][C:14]=1[C:15]#[N:16]>C(Cl)Cl>[F:12][C:13]1[C:20]([O:21][CH3:22])=[C:19]([CH:23]2[CH2:24][O:9]2)[CH:18]=[CH:17][C:14]=1[C:15]#[N:16]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86727088HCID 86727088, compound

Product 1

HCID 86727089HCID 86727089, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

mCPBA (85%, 9.9 g, 48.9 mmol) was added to the solution of 2-fluoro-3-methoxy-4-vinylbenzonitrile (3.4 g, 19.2 mmol) in 160 mL of DCM at 0° C. The mixture was stirred at room temperature for 60 hours before being diluted with 300 mL of DCM and cooled to 0° C. The mixture was washed subsequently with saturated NaHCO3 (50 mL), aqueous Na2SO3 (2×50 mL), 5% NaOH (50 mL) and brine. The organic layer was concentrated, and the residue was purified by column chromatography (PE:EtOAc=5:1) to afford 2-fluoro-3-methoxy-4-(oxiran-2-yl)benzonitrile: 1H NMR (400 MHz, CDCl3) δ 7.24 (d, J=7.6 Hz, 1H), 6.98 (d, J=7.6 Hz, 1H), 4.14-4.18 (m, 1H), 4.03 (s, 3H), 3.17-3.19 (m, 1H), 2.63-2.66 (m, 1H); MS m/z 194 (M+1)+.

Workup

  1. temperaturecooled to 0° C
  2. washThe mixture was washed subsequently with saturated NaHCO3 (50 mL), aqueous Na2SO3 (2×50 mL), 5% NaOH (50 mL) and brine
  3. concentrationThe organic layer was concentrated
  4. customthe residue was purified by column chromatography (PE:EtOAc=5:1)

Sources & evidence

ORD record
ord-b0964415fb694a1caebfcb2ffc46d42f
Source dataset
uspto-grants-2015_06
Patent number
US09062070B2

Reaction notes

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