Methanesulfonyl chloride → 2-(4-Cyano-3-fluorophenyl)ethyl methanesulfonate

HRID 1187011Notes

Reaction equation

HRID 1187011 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([CH2:10][CH2:11][OH:12])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH3:13][S:14](Cl)(=[O:16])=[O:15]>C(Cl)Cl>[CH3:13][S:14]([O:12][CH2:11][CH2:10][C:8]1[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([F:1])[CH:9]=1)(=[O:16])=[O:15]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 666441972-Fluoro-4-(2-hydroxyethyl)benzonitrile

Product 1

HCID 866473092-(4-Cyano-3-fluorophenyl)ethyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-fluoro-4-(2-hydroxyethyl)benzonitrile (22.5 g, 136 mmol) and MsCl (23.3 g, 205 mmol) in 200 mL of dry DCM was added dropwise TEA (27.5 g, 273 mmol) at 0° C. The resulting mixture was stirred at room temperature overnight before concentrating to dryness. The residue was dissolved in 300 mL of EtOAc and washed with 1 N HCl and brine, dried over anhydrous Na2SO4 and concentrated to afford crude 2-(4-cyano-3-fluorophenyl)ethyl methanesulfonate. MS m/z 244 (M+1)+.

Workup

  1. concentrationbefore concentrating to dryness
  2. dissolutionThe residue was dissolved in 300 mL of EtOAc
  3. washwashed with 1 N HCl and brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-102559ab846b48bbb257878be7503a62
Source dataset
uspto-grants-2014_03
Patent number
US08673920B2

Reaction notes

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