m-Chloroperbenzoic acid → HCID 86696908, compound

HRID 1399997Notes

Reaction equation

HRID 1399997 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([C:8]2[CH2:9][CH2:10][O:11][CH2:12][CH:13]=2)=[N:6][CH:7]=1.ClC1C=C(C(OO)=[O:22])C=CC=1>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[N:4][C:5]([C:8]23[O:22][CH:9]2[CH2:10][O:11][CH2:12][CH2:13]3)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 86696907HCID 86696907, compound

Product 1

HCID 86696908HCID 86696908, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Compound i (105 mg; 0.436 mmol) was dissolved in DCM (15 mL) and cooled to 0° C., then solid 3-chlorobenzenecarboperoxoic acid (280 mg, 1.14 mmol) was added and the mixture stirred overnight. The mixture was quenched with 1M Na2S2O3 (aq) (5 mL), washed with sat. NaHCO3 (aq) (3×30 mL) followed by brine (1×30 mL). The organic fraction was dried (MgSO4). Purification by chromatography on silica eluting with 0-50% EtOAc-n-heptane gave ii (20 mg, 18%). MS: 256.9 & 258.8; 1:1 [M+H]+.

Workup

  1. customThe mixture was quenched with 1M Na2S2O3 (aq) (5 mL)
  2. washwashed with sat. NaHCO3 (aq) (3×30 mL)
  3. dry with materialThe organic fraction was dried (MgSO4)
  4. customPurification by chromatography on silica eluting with 0-50% EtOAc-n-heptane

Sources & evidence

ORD record
ord-447094b35692418d99ef66f3dd029207
Source dataset
uspto-grants-2014_12
Patent number
US08906902B2

Reaction notes

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