Triethylamine → 4-Cyano-2,5-difluorobenzyl methanesulfonate

HRID 1990765Notes

Reaction equation

HRID 1990765 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([CH2:10][OH:11])[C:7]([F:12])=[CH:6][C:3]=1[C:4]#[N:5].[CH3:13][S:14](Cl)(=[O:16])=[O:15].C(N(CC)CC)C>C(Cl)Cl>[CH3:13][S:14]([O:11][CH2:10][C:8]1[CH:9]=[C:2]([F:1])[C:3]([C:4]#[N:5])=[CH:6][C:7]=1[F:12])(=[O:16])=[O:15]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 219046532,5-Difluoro-4-(hydroxymethyl)benzonitrile

Product 1

HCID 219046244-Cyano-2,5-difluorobenzyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice cooled solution of 2,5-difluoro-4-hydroxymethylbenzonitrile (3.10 g, 0.0183 mol; see step (iii) above) and methanesulfonyl chloride (2.21 g, 0.0192 mol) in 60 mL of methylene chloride was added triethyl amine (1.95 g, 0.0192 mol) with stirring. After 1.5 h at 0° C. the mixture was washed with water, dried (Na2SO4) and evaporated. The product could be used without further purification. Yield: 4.5 g (99%).

Workup

  1. washAfter 1.5 h at 0° C. the mixture was washed with water
  2. dry with materialdried (Na2SO4)
  3. customevaporated
  4. customThe product could be used without further purification

Sources & evidence

ORD record
ord-f68d060dd3e743d7be0944413803fd32
Source dataset
uspto-grants-2010_01
Patent number
US07645751B2

Reaction notes

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