Triethylamine → Methanesulfonic acid 4-fluoro-5-iodo-2-methanesulfonyloxymethyl-benzyl ester

HRID 225672Notes

Reaction equation

HRID 225672 reaction equation
[F:1][C:2]1[C:3]([I:12])=[CH:4][C:5]([CH2:10][OH:11])=[C:6]([CH2:8][OH:9])[CH:7]=1.C(N(CC)CC)C.[CH3:20][S:21](Cl)(=[O:23])=[O:22]>ClCCl.O>[F:1][C:2]1[C:3]([I:12])=[CH:4][C:5]([CH2:10][O:11][S:21]([CH3:20])(=[O:23])=[O:22])=[C:6]([CH2:8][O:9][S:21]([CH3:20])(=[O:23])=[O:22])[CH:7]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 57753608(5-Fluoro-2-hydroxymethyl-4-iodo-phenyl)-methanol

Product 1

HCID 57753243Methanesulfonic acid 4-fluoro-5-iodo-2-methanesulfonyloxymethyl-benzyl esterYield 67%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of 8.86 mmol (5-fluoro-2-hydroxymethyl-4-iodo-phenyl)-methanol in 30 ml dichloromethane at 0° C. were added dropwise 22.2 mmol triethylamine and 19.5 mmol methanesulfonyl chloride. The mixture was stirred at 0° C. for 1 h, and then at room temperature for 5 h. The reaction mixture was diluted with water and extracted four times with dichloromethane. The combined organic phases were dried over sodium sulfate and concentrated in vacuo to afford the title compound as a yellow oil (67% yield) which was used in the next step without further purification.

Workup

  1. waitat room temperature for 5 h
  2. extractionextracted four times with dichloromethane
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-07af760e6a8c43198d5ef0a8f63245b1
Source dataset
uspto-grants-2009_07
Patent number
US07557114B2

Reaction notes

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