Triethylamine → Methanesulfonic acid 2-(4-fluoro-2-methoxy-phenyl)-ethyl ester

HRID 1350064Notes

Reaction equation

HRID 1350064 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[C:4]([O:11][CH3:12])[CH:3]=1.C(N(CC)CC)C.[CH3:20][S:21](Cl)(=[O:23])=[O:22]>ClCCl.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][O:10][S:21]([CH3:20])(=[O:23])=[O:22])=[C:4]([O:11][CH3:12])[CH:3]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 178581442-(4-Fluoro-2-methoxyphenyl)ethan-1-ol

Product 1

HCID 86596745Methanesulfonic acid 2-(4-fluoro-2-methoxy-phenyl)-ethyl esterYield 100%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 5.1 g (29.97 mmol) of 2-(4-Fluoro-2-methoxy-phenyl)-ethanol in 30 ml of anhydrous dichloromethane was added at 0° C. 6.26 ml (44.95 mmol) of triethylamine and 3.5 ml (44.95 mmol) of methanesulfonyl chloride. The resulting mixture was stirred at 0° C. for 1 h. The mixture was then diluted with water and dichloromethane and extracted with dichloromethane. Organic layer was dried and evaporated to give 7 g(100%) of methanesulfonic acid 2-(4-fluoro-2-methoxy-phenyl)-ethyl ester.

Workup

  1. extractionextracted with dichloromethane
  2. customOrganic layer was dried
  3. customevaporated

Sources & evidence

ORD record
ord-1280bce6704b4f8d971670afabd6ffd5
Source dataset
uspto-grants-2007_05
Patent number
US07214682B2

Reaction notes

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