Water → 1-(Methanesulfonylmethyl)-3-nitrobenzene

HRID 514693Notes

Reaction equation

HRID 514693 reaction equation
ClC1C=C(C(OO)=[O:9])C=CC=1.[CH3:12][S:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=1.C(=O)(O)[O-].[Na+].[OH2:29]>C(Cl)Cl>[CH3:12][S:13]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-:23])=[O:22])[CH:16]=1)(=[O:9])=[O:29]

Participants

6

Reactant 4

HCID 962WaterHCID 70297m-Chloroperbenzoic acidHCID 516892Sodium BicarbonateHCID 22031873Methyl(3-nitrobenzyl)sulfane

Product 1

HCID 179084331-(Methanesulfonylmethyl)-3-nitrobenzene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

3-Chlorobenzenecarboperoxoic acid (77%; 26.9 g; 120 mmol) was added to a stirred solution of 1-[(methylsulfanyl)methyl]-3-nitrobenzene (10.0 g) in DCM (1305 mL) at 0° C. The batch was stirred at 0° C. for 30 minutes and then 2.5 hours at room temperature. The batch was diluted with water (300 mL) before sodium bicarbonate (11.0 g) was added. The batch was extracted with DCM (2×). The combined organic phases were filtered using a Whatman filter and concentrated. The residue was purified by chromatography (DCM/ethanol 95:5) and finally recrystallized from ethyl acetate to give the desired product (6.2 g; 28.9 mmol).

Workup

  1. custom2.5 hours
  2. customat room temperature
  3. additionwas added
  4. extractionThe batch was extracted with DCM (2×)
  5. filtrationThe combined organic phases were filtered
  6. filtrationfilter
  7. concentrationconcentrated
  8. customThe residue was purified by chromatography (DCM/ethanol 95:5)
  9. customfinally recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-5a2723e22f674246a963491f0d427b08
Source dataset
uspto-grants-2015_08
Patent number
US09108926B2

Reaction notes

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