Cesium carbonate → t-Butyl 2-(2-(4-fluoro-3-(methylsulfonyl)phenyl)-4-formylphenoxy)acetate

HRID 68610Notes

Reaction equation

HRID 68610 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=2[OH:16])[CH:11]=[O:12])=[CH:4][C:3]=1[S:17]([CH3:20])(=[O:19])=[O:18].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30]>CN(C=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]([CH:11]=[O:12])[CH:13]=[CH:14][C:15]=2[O:16][CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[CH:4][C:3]=1[S:17]([CH3:20])(=[O:18])=[O:19]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 79177tert-Butyl bromoacetateHCID 866818403-(4-Fluoro-3-(methylsulfonyl)phenyl)-4-hydroxybenzaldehyde

Product 1

HCID 86681841t-Butyl 2-(2-(4-fluoro-3-(methylsulfonyl)phenyl)-4-formylphenoxy)acetateYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(4-fluoro-3-(methylsulfonyl)phenyl)-4-hydroxybenzaldehyde (28) (315 mg, 1.1 mmol, 1 eq.) in DMF (10 mL) was added Cs2CO3 (715 mg, 2.2 mmol, 2 eq.) and t-butyl 2-bromoacetate (236 mg, −1.2 mmol, 1.2 eq.). After stirring at room temperature, for 16 h, the solvent was removed in vacuo, and the resultant residue was extracted between EtOAc and H2O (3×20 mL). The organic layer was dried (Na2SO4), and concentrated in vacuo. The resultant residue was purified by column chromatography (eluent: PE:EA=1:1) to give 250 mg (57%) of t-butyl 2-(2-(4-fluoro-3-(methylsulfonyl)phenyl)-4-formylphenoxy)acetate (29) as oil.

Workup

  1. customthe solvent was removed in vacuo
  2. extractionthe resultant residue was extracted between EtOAc and H2O (3×20 mL)
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. customThe resultant residue was purified by column chromatography (eluent: PE:EA=1:1)

Sources & evidence

ORD record
ord-ec063406d5954c2aa4ef11061dc042ba
Source dataset
uspto-grants-2014_09
Patent number
US08822467B2

Reaction notes

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