Pyridine → 3-Nitrophenethyl methanesulfonate

HRID 2370498Notes

Reaction equation

HRID 2370498 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]>ClCCl>[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][CH2:11][O:12][S:20]([CH3:19])(=[O:22])=[O:21])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 1040583-Nitrophenylethyl alcohol

Product 1

HCID 219738843-Nitrophenethyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 2-(3-nitro-phenyl)-ethanol (1 eq) in dichloromethane at 0° C. was added pyridine (4 eq) and methanesulfonyl chloride (2 eq). After stirring at 0° C. for one hour, then room temperature overnight, the mixture was diluted with dichloromethane and washed once with water, once with 1 N HCl, dried with anhydrous sodium sulfate, filtered and concentrated. The product was clean enough to be taken on to the next step without purification. MH+=246.0.

Workup

  1. washwashed once with water, once with 1 N HCl
  2. dry with materialdried with anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto be taken on to the next step without purification

Sources & evidence

ORD record
ord-8e9d0aac25d94416b31b2cd6f01eee87
Source dataset
uspto-grants-2014_04
Patent number
US08710048B2

Reaction notes

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