Water → 1-Bromo-4-(ethanesulfonyl)benzene

HRID 2387030Notes

Reaction equation

HRID 2387030 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][CH2:9][CH3:10])=[CH:4][CH:3]=1.[Mn]([O-])(=O)(=O)=[O:12].[K+].[OH2:17]>C(O)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH2:9][CH3:10])(=[O:12])=[O:17])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 516875Potassium PermanganateHCID 70066501-Bromo-4-(ethylthio)benzene

Product 1

HCID 115723521-Bromo-4-(ethanesulfonyl)benzene

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
90 °C

Procedure

1-Bromo-4-ethylsulfanyl-benzene (5.0 g) was dissolved in acetic acid and potassium permanganate as a 3% solution in water (8 mL) was added. The reaction mixture was heated to 90° C. for 3 hrs, after which time the reaction was cooled to room temperature and partitioned between ethyl acetate and 2N NaOH solution (500 m) each. The organics were separated and washed with water (100 mL), dried over sodium sulfate and purified on biotage eluting with 90:10 hexanes:ethyl acetate to afford the title compound as a clear oil (2.70 g). 1H NMR (300 MHz, CDCl3): δ 1.30 (t, J=7.85 Hz, 3 H) 3.02 (q, J=7.54 Hz, 2 H), 7.40 (m, 4 H).

Workup

  1. temperatureafter which time the reaction was cooled to room temperature
  2. custompartitioned between ethyl acetate and 2N NaOH solution (500 m) each
  3. customThe organics were separated
  4. washwashed with water (100 mL)
  5. dry with materialdried over sodium sulfate
  6. custompurified on biotage
  7. washeluting with 90:10 hexanes

Sources & evidence

ORD record
ord-8a39b6897305464299ff1ffd00fbf8a8
Source dataset
uspto-grants-2012_09
Patent number
US08268835B2

Reaction notes

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