Hydrogen Peroxide → HCID 58442391, compound

HRID 1465656Notes

Reaction equation

HRID 1465656 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[C:10]([CH3:11])=[CH:9][C:8]([S:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)=[CH:7][C:6]=1[CH3:21])=[O:4].C(OC(=O)C)(=[O:24])C.OO>ClCCl>[Br:1][CH2:2][C:3]([C:5]1[C:6]([CH3:21])=[CH:7][C:8]([S:12]([C:13]2[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=2)=[O:24])=[CH:9][C:10]=1[CH3:11])=[O:4]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 7918Acetic AnhydrideHCID 58442547HCID 58442547, compound

Product 1

HCID 58442391HCID 58442391, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-bromo-1-(4-(4-methoxyphenylthio)-2,6-dimethylphenyl)ethanone (500.0 mg, 1.3 mmol, 1.0 equiv), acetic anhydride (0.14 mL, 1.5 mmol, 1.1 equiv), 30% hydrogen peroxide (55.86 mg, 1.6 nm 101, 1.2 equiv) and silica gel (273.75 mg, 230-400 mesh) in dichloromethane (10.0 mL) was stirred at room temperature for 16 h. The solution was concentrated under reduced pressure, and the residue was re-dissolved in EtOAc (50 mL). The solution was washed with saturated aqueous NaHCO3 (30 mL), dried over MgSO4(s), and concentrated under reduced pressure to give 2-bromo-1-(4-(4 methoxyphenylsulfinyl)-2,6-dimethylphenyl)ethanone (235.4 mg, 0.6 mmol) as pale yellow oil in 48% yield: 1H NMR (DMSO-d6, 500 MHz) δ 7.65 (d, J=8.8 Hz, 2 H), 7.41 (s, 2 H), 7.09 (d, J=8.8 Hz, 2 H), 4.78 (s, 2 H), 3.79 (s, 3 H), 2.21 (s, 6 H).

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. dissolutionthe residue was re-dissolved in EtOAc (50 mL)
  3. washThe solution was washed with saturated aqueous NaHCO3 (30 mL)
  4. dry with materialdried over MgSO4(s)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-21008e705a5a43a8bb2fc4eef2c20eaa
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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