Benzoyl Peroxide → HCID 59610060, compound

HRID 1889165Notes

Reaction equation

HRID 1889165 reaction equation
[CH3:1][O:2][C:3](=[O:20])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)(=[O:13])=[O:12])=[CH:7][CH:6]=1.C1C(=O)N([Br:28])C(=O)C1.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl.C(Cl)Cl>[CH3:1][O:2][C:3](=[O:20])[CH:4]([Br:28])[C:5]1[CH:10]=[CH:9][C:8]([S:11]([CH:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)(=[O:12])=[O:13])=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 7187Benzoyl PeroxideHCID 67184N-bromobutanimideHCID 59610035HCID 59610035, compound

Product 1

HCID 59610060HCID 59610060, compoundYield 37.1%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 6344DichloromethaneSolvent

Procedure

[4-(Tetrahydro-pyran-4-sulfonyl)-phenyl]-acetic acid methyl ester (1.60 gm, 5.36 mmol), NBS (1.04 g, 5.90 mmol) and benzoyl peroxide (0.130 g, 0.53 mmol) in carbon tetrachloride (50 ml) was refluxed for 7 hrs. Reaction mixture was diluted with DCM (50 ml), washed with water and brine (100 ml each), dried over anhydrous sodium sulfate, fliltered and concentrated. Crude compound was purified by column chromatography over silica gel using 30% ethyl acetate hexane as eluent to give the pure bromo-[4-(tetrahydro-pyran-4-sulfonyl)-phenyl]-acetic acid methyl ester (0.75 gm).

Workup

  1. customReaction mixture
  2. washwashed with water and brine (100 ml each)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated
  5. customCrude compound was purified by column chromatography over silica gel using 30% ethyl acetate hexane as eluent

Sources & evidence

ORD record
ord-3858e3980014430daaaf6fc249519bec
Source dataset
uspto-grants-2013_08
Patent number
US08501955B2

Reaction notes

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