m-Chloroperbenzoic acid → HCID 17756176, compound

HRID 1723995Notes

Reaction equation

HRID 1723995 reaction equation
[CH3:1][C:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[O:4][C:3]=1[S:13][CH3:14].C1C=C(Cl)C=C(C(OO)=[O:23])C=1>ClCCl>[CH3:14][S:13]([C:3]1[O:4][C:5]2[C:10]([C:11](=[O:12])[C:2]=1[CH3:1])=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:23]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 57436867HCID 57436867, compound

Product 1

HCID 17756176HCID 17756176, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution containing 3-methyl-2-methylsulfanyl-chromen-4-one (1.95 g, 9.45 mmol) in dichloromethane (75 mL) at 0° C. was added mCPBA (2 g, 11.82 mmol). The reaction stirred for 2 hours. After consumption of the starting material, the reaction mixture was filtered and the resulting filtrate was washed with cold 5% sodium carbonate, water, and saturated sodium bisulfate. The organic layer was dried over sodium sulfate, filtered, and concentrated to obtain the desired product as a light yellow solid (1.74 g, 83% yield), which was taken on to the next step without further purification. 1H NMR (600 MHz, DMSO-d6): δ 8.08 (dd, 1H, J=7.8, 1.2 Hz), 7.88 (m, 1H), 7.76 (d, 1H, J=7.8 Hz), 7.55 (m, 1H), 3.01 (s, 3H), 2.12 (s, 3H).

Workup

  1. customAfter consumption of the starting material
  2. filtrationthe reaction mixture was filtered
  3. washthe resulting filtrate was washed with cold 5% sodium carbonate, water, and saturated sodium bisulfate
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9710dfef70bc44059876b6a99fa13ce5
Source dataset
uspto-grants-2009_02
Patent number
US07485283B2

Reaction notes

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