Potassium Carbonate → [4-Chloro-2-[[4-(ethylsulfonyl)phenyl]thio]phenoxy]-acetic acid, 1,1-dimethylethyl ester

HRID 1945187Notes

Reaction equation

HRID 1945187 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([S:9][C:10]2[CH:15]=[CH:14][C:13]([S:16]([CH2:19][CH3:20])(=[O:18])=[O:17])=[CH:12][CH:11]=2)[CH:3]=1.[C:21]([O:25][C:26](=[O:29])[CH2:27]Br)([CH3:24])([CH3:23])[CH3:22].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:27][C:26]([O:25][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:29])=[C:4]([S:9][C:10]2[CH:11]=[CH:12][C:13]([S:16]([CH2:19][CH3:20])(=[O:17])=[O:18])=[CH:14][CH:15]=2)[CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 669960804-Chloro-2-[[4-(ethylsulfonyl)phenyl]thio]-phenol

Product 1

HCID 86659304[4-Chloro-2-[[4-(ethylsulfonyl)phenyl]thio]phenoxy]-acetic acid, 1,1-dimethylethyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of the product from step (iii) (0.3 g), tert-butylbromoacetate (0.15 ml) and potassium carbonate (0.13 g) in DMF (20 ml) was stirred at RT overnight. The mixture was partitioned between water and ethylacetate, the organics separated, dried, and evaporated under reduced pressure. Yield 0.55 g

Workup

  1. customThe mixture was partitioned between water and ethylacetate
  2. customthe organics separated, dried
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-bf0738449cd443e38942eb8572d0aff4
Source dataset
uspto-grants-2013_03
Patent number
US08394986B2

Reaction notes

Loading…