Hydrochloric Acid → 2-Fluorodecyl p-toluenesulfonate

HRID 1728512Notes

Reaction equation

HRID 1728512 reaction equation
[F:1][CH:2]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])[CH2:3][OH:4].N1C=CC=CC=1.[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25](Cl)(=[O:27])=[O:26])=[CH:21][CH:20]=1.Cl>O>[C:19]1([CH3:29])[CH:24]=[CH:23][C:22]([S:25]([O:4][CH2:3][CH:2]([F:1])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])(=[O:27])=[O:26])=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 110844191-Decanol, 2-fluoro-

Product 1

HCID 189458582-Fluorodecyl p-toluenesulfonateYield 72.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

17 g of 2-fluorodecanol and 60 ml of pyridine were charged into a 300 ml three-necked round bottom flask and cooled to 0° C. to which 24 g of p-toluenesulfonyl chloride was added in 15 min. The system was held at 0° C. for 1 hour and then subjected to reaction for 7 hours while being held below 20° C. Then, the mixture was charged into water and acidified with hydrochloric acid, followed by extraction with dichloromethane. The organic layer was washed with water, dried with magnesium sulfate and then purified by silica gel chromatography with the use of dichloromethane as the eluent to obtain 23 g of 2-fluorodecyl p-toluenesulfonate.

Workup

  1. additionwas added in 15 min
  2. customsubjected to reaction for 7 hours
  3. customwhile being held below 20° C
  4. extractionfollowed by extraction with dichloromethane
  5. washThe organic layer was washed with water
  6. dry with materialdried with magnesium sulfate
  7. custompurified by silica gel chromatography with the use of dichloromethane as the eluent

Sources & evidence

ORD record
ord-112d56e2206a4530aa19d7749bec2253
Source dataset
uspto-grants-1994_07
Patent number
US05328639

Reaction notes

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