Methanesulfonyl chloride → [4-chloro-2-(1-chloroethyl)phenoxy]-acetic Acid, 1,1-dimethylethyl Ester

HRID 38260Notes

Reaction equation

HRID 38260 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]([CH:17](O)[CH3:18])[CH:3]=1.CCN(C(C)C)C(C)C.CS([Cl:33])(=O)=O>C(Cl)Cl>[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]([CH:17]([Cl:33])[CH3:18])[CH:3]=1

Participants

5

Reactant 3

HCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 86631057[4-chloro-2-(1-hydroxyethyl)phenoxy]-acetic Acid, 1,1-dimethylethyl Ester

Product 1

HCID 86631056[4-chloro-2-(1-chloroethyl)phenoxy]-acetic Acid, 1,1-dimethylethyl Ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the product of step b) (0.34 g) in DCM (5 ml) was added Hunigs base (1 ml) followed by methanesulfonyl chloride (0.46 ml) and the reaction stirred at room temperature for 2 h followed by heating at 45° C. for 2 h. After cooling to 0° C. the bulk of the volatiles were removed in vacuo. Diethyl ether and water were added and the organic layer separated.

Workup

  1. temperatureby heating at 45° C. for 2 h
  2. temperatureAfter cooling to 0° C. the bulk of the volatiles
  3. customwere removed in vacuo
  4. additionDiethyl ether and water were added
  5. customthe organic layer separated

Sources & evidence

ORD record
ord-751bf4b766aa40ed99c35ebfb6283106
Source dataset
uspto-grants-2013_09
Patent number
US08524715B2

Reaction notes

Loading…