Water → 1-(Methanesulfonylmethyl)-3-nitrobenzene

HRID 1405169Notes

Reaction equation

HRID 1405169 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 combinded 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 combinded 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-b3f5709b432f4b57aee928ad63ca5ae3
Source dataset
uspto-grants-2014_12
Patent number
US08916557B2

Reaction notes

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