m-Chloroperbenzoic acid → HCID 89621411, compound

HRID 536465Notes

Reaction equation

HRID 536465 reaction equation
[Br:1][C:2]1[C:3]([F:11])=[CH:4][CH:5]=[C:6]2[C:10]=1[CH2:9][CH:8]=[CH:7]2.C1C=C(Cl)C=C(C(OO)=[O:20])C=1>ClCCl>[Br:1][C:2]1[C:10]2[CH2:9][CH:8]3[O:20][CH:7]3[C:6]=2[CH:5]=[CH:4][C:3]=1[F:11]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 684592997-Bromo-6-fluoro-1H-indene

Product 1

HCID 89621411HCID 89621411, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of Example 25C (500 mg, 2.347 mmol) in dichloromethane (30 mL) was cooled to 0° C. and a solution of mCPBA (631 mg, 2.82 mmol) in dichloromethane (5 mL) was added. The mixture was warmed to ambient temperature and stirred for 2 hours. The mixture was diluted with dichloromethane (50 mL), quenched with a saturated solution of Na2S2O3 and partitioned. The organic portion was dried (MgSO4), filtered, concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (elution with 10% EtOAc/hexanes) to provide the title product (316 mg, 1.38 mmol, 59%). MS (DCI) m/z 230 (M+H)+.

Workup

  1. customquenched with a saturated solution of Na2S2O3
  2. custompartitioned
  3. dry with materialThe organic portion was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel chromatography (elution with 10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-e096842611504323aed62d2138f12d97
Source dataset
uspto-grants-2014_10
Patent number
US08859584B2

Reaction notes

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