Water → 3-Nitrophenethyl methanesulfonate

HRID 1256154Notes

Reaction equation

HRID 1256154 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][CH2:11][OH:12])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].N1C=CC=CC=1.[CH3:19][S:20](Cl)(=[O:22])=[O:21].O>C(Cl)Cl>[CH3:19][S:20]([O:12][CH2:11][CH2:10][C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)(=[O:22])=[O:21]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 1040583-Nitrophenylethyl alcohol

Product 1

HCID 219738843-Nitrophenethyl methanesulfonateYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(3-nitrophenyl)ethanol (9 g, 53.8 mmol) in DCM (100 mL) was cooled to 0° C., then pyridine (22.7 g, 287 mmol) was dropwise added to the reaction solution. Then methylsulfonylchloride was added slowly dropwise, followed by stirring at room temperature for one hour. Water was added to terminate the reaction. The aqueous layer was extracted by ethyl acetate 3 times. The combined organic phase was washed with brine, dried over sodium sulfate and concentrated to give 3-nitrophenethyl methanesulfonate (13 g, yield 98%). 1H NMR: 400 MHz CDCl3 δ 8.13-8.10 (m, 2H), 7.60-7.53 (m, 1H), 7.53-7.47 (m, 1H), 4.48-4.45 (m, 2H), 3.19-3.15 (m, 2H), 2.95 (s, 3H).

Workup

  1. customto terminate
  2. customthe reaction
  3. extractionThe aqueous layer was extracted by ethyl acetate 3 times
  4. washThe combined organic phase was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c0d26842476842b6bb65ed40f7d9aa4e
Source dataset
uspto-grants-2013_06
Patent number
US08461134B2

Reaction notes

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