Methanesulfonyl chloride → HCID 18924794, compound

HRID 1428706Notes

Reaction equation

HRID 1428706 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][OH:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:12][S:13](Cl)(=[O:15])=[O:14]>C1(C)C=CC=CC=1>[CH3:12][S:13]([O:11][CH2:10][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=1)(=[O:15])=[O:14]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 692754-Nitrobenzyl alcohol

Product 1

HCID 18924794HCID 18924794, compoundYield 72.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (4-nitrophenyl)methanol (2 g, 13.06 mmol) in toluene (10 mL) was slowly added methane sulfonylchloride (1.21 mL, 15.67 mmol) at room temperature. The reaction mixture was heated to 80° C. for 4 h. TLC showed complete consumption of starting material. The reaction mixture was cooled to room temperature. The mixture was extracted with ethyl acetate and washed with water and brine. The extract was dried over magnesium sulfate and concentrated under reduced pressure. The crude was purified by column chromatography to give 4-nitrobenzyl methanesulfonate (2.2 g, 72%).

Workup

  1. customat room temperature
  2. customconsumption of starting material
  3. temperatureThe reaction mixture was cooled to room temperature
  4. extractionThe mixture was extracted with ethyl acetate
  5. washwashed with water and brine
  6. dry with materialThe extract was dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe crude was purified by column chromatography

Sources & evidence

ORD record
ord-7c882cb5e8844d5eae5059e6db5d9022
Source dataset
uspto-grants-2015_01
Patent number
US08937092B2

Reaction notes

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