m-Chloroperbenzoic acid → HCID 25115686, compound

HRID 2194625Notes

Reaction equation

HRID 2194625 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[Cl:12][C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1[C:20]1[C:21]2[CH:29]=[CH:28][N:27]=[C:26]([C:30]3[C:35]([F:36])=[CH:34][CH:33]=[CH:32][C:31]=3[F:37])[C:22]=2[N:23]=[CH:24][N:25]=1>ClCCl>[Cl:12][C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1[C:20]1[C:21]2[CH:29]=[CH:28][N+:27]([O-:9])=[C:26]([C:30]3[C:35]([F:36])=[CH:34][CH:33]=[CH:32][C:31]=3[F:37])[C:22]=2[N:23]=[CH:24][N:25]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 25115685HCID 25115685, compound

Product 1

HCID 25115686HCID 25115686, compoundYield 47.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Meta-chloroperbenzoic acid (77%) (30 mg, 0.13 mmol) was added portionwise to a solution of the title compound from Example 25 (50 mg, 0.13 mmol) in dichloromethane (2.5 mL) at 0° C. and the reaction mixture was stirred overnight at room temperature. Then, more dichloromethane was added (50 mL) and the solution was washed with 1N NaOH (2×30 ml) and brine. The organic layer was dried over sodium sulphate and concentrated under reduced pressure to yield an oil which was purified by column chromatography on silica gel, using hexane/ethyl acetate (5:1) as eluent, to yield the title compound (24 mg, 46%) as an off-white solid.

Workup

  1. washthe solution was washed with 1N NaOH (2×30 ml) and brine
  2. dry with materialThe organic layer was dried over sodium sulphate
  3. concentrationconcentrated under reduced pressure
  4. customto yield an oil which
  5. customwas purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-b2750f8bd24b49238757edcc2c5572d1
Source dataset
uspto-grants-2012_12
Patent number
US08334294B2

Reaction notes

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