Triethylamine → 4-Cyano-3-fluorobenzyl methanesulfonate

HRID 1990754Notes

Reaction equation

HRID 1990754 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([CH2:10][OH:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].C(N(CC)CC)C.[CH3:19][S:20](Cl)(=[O:22])=[O:21]>C(Cl)Cl>[CH3:19][S:20]([O:11][CH2:10][C:8]1[CH:7]=[CH:6][C:3]([C:4]#[N:5])=[C:2]([F:1])[CH:9]=1)(=[O:22])=[O:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 118296312-Fluoro-4-(hydroxymethyl)benzonitrile

Product 1

HCID 219046204-Cyano-3-fluorobenzyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Fluoro-4-hydroxymethylbenzonitrile (1.3 g, 8.6 mmol; see step (ii) above) was dissolved in 50 mL of CH2Cl2 and cooled on an ice bath. Triethylamine (0.87 g, 8.6 mmol) and methanesulfonyl chloride (0.99 g, 8.7 mmol) were added. After stirring for 1.5 h the reaction mixture was washed with 1M HCl. The organic phase was dried (Na2SO4) and evaporated. The product could be used without purification. Yield of a colourless oil: 1.8 g (92%).

Workup

  1. temperaturecooled on an ice bath
  2. washwas washed with 1M HCl
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. customevaporated
  5. customThe product could be used without purification

Sources & evidence

ORD record
ord-6014d9071b9342bb88d685c63048d561
Source dataset
uspto-grants-2010_01
Patent number
US07645751B2

Reaction notes

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