m-Chloroperbenzoic acid → HCID 68864539, compound

HRID 1725941Notes

Reaction equation

HRID 1725941 reaction equation
[Br:1][C:2]1[C:11]2[C:10]([CH3:12])=[CH:9][CH2:8][CH2:7][C:6]=2[CH:5]=[CH:4][C:3]=1[NH:13][S:14]([C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)(=[O:16])=[O:15].C1C=C(Cl)C=C(C(OO)=[O:32])C=1>C(Cl)Cl.C(OCC)(=O)C.C(OCC)C.[I-].[Zn+2].[I-]>[Br:1][C:2]1[C:11]2[CH:10]([CH3:12])[C:9](=[O:32])[CH2:8][CH2:7][C:6]=2[CH:5]=[CH:4][C:3]=1[NH:13][S:14]([C:17]1[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=1)(=[O:16])=[O:15]

Participants

7

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 68865166HCID 68865166, compound

Product 1

HCID 68864539HCID 68864539, compoundYield 79%

Reagents, catalysts & solvents 4

HCID 9883512zinc(II)iodideCatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of Example 132A (170 mg, 0.43 mmol) in CH2Cl2 (5 mL) at 0° C. was treated with mCPBA (136 mg, 0.47 mmol), warmed to room temperature, stirred for 2 hours, diluted with ethyl acetate, washed with NaHCO3 and brine, dried (Na2SO4), filtered, and concentrated. The concentrate was dissolved in toluene (5 mL), treated with activated-zinc iodide (37 mg, 0.12 mmol), heated to reflux for 1 hour, diluted with diethyl ether, washed with brine, dried (Na2SO4), filtered, and concentrated to provide the desired product (140 mg, 79% yield). MS (ESI) m/e 410 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 9.92 (s, 1H), 7.73 (m, 2H), 7.4 (m, 2H), 7.24 (d, 1H), 7.0 (d, 1H), 3.6 (q, 1H), 3.15 (m, 1H), 2.93 (m, 1H), 2.59 (m, 1H), 2.41 (m, 1H), 1.2 (d, 3H).

Workup

  1. washwashed with NaHCO3 and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. dissolutionThe concentrate was dissolved in toluene (5 mL)
  6. temperatureheated
  7. temperatureto reflux for 1 hour
  8. washwashed with brine
  9. dry with materialdried (Na2SO4)
  10. filtrationfiltered
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-74603ebe066a4ae7a82203342a3fa405
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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