Triethylamine → [4-chloro-2-[[(methylsulfonyl)oxy]methyl]phenoxy]-acetic Acid, 1,1-dimethylethyl Ester

HRID 38288Notes

Reaction equation

HRID 38288 reaction equation
[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[C:4]([CH2:17][OH:18])[CH:3]=1.C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>ClCCl>[Cl:1][C:2]1[CH:16]=[CH:15][C:5]([O:6][CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:12])[CH3:13])=[O:9])=[C:4]([CH2:17][O:18][S:27]([CH3:26])(=[O:29])=[O:28])[CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 86631069[4-chloro-2-(hydroxymethyl)phenoxy]-acetic Acid, 1,1-dimethylethyl Ester

Product 1

HCID 86631070[4-chloro-2-[[(methylsulfonyl)oxy]methyl]phenoxy]-acetic Acid, 1,1-dimethylethyl Ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of the product of part (d) (1 g) and triethylamine (0.51 ml) in dichloromethane (10 ml) was cooled to 0° C. Methanesulfonyl chloride (0.29 ml) was then added dropwise and the reaction was allowed to reach room temperature. After stirring for 3 hours the reaction was diluted with dichloromethane, washed with water, NaHCO3 (aq), brine, dried (MgSO4) and concentrated in vacuo to give the subtitle compound as an oil (1.13 g).

Workup

  1. customto reach room temperature
  2. washwashed with water, NaHCO3 (aq), brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-afe80fed5d1946bf9d4f7a78e1dc5bdf
Source dataset
uspto-grants-2013_09
Patent number
US08524715B2

Reaction notes

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