Cesium carbonate → 2-(4-Chloro-2-formyl-phenoxy)-2-methyl-propionic acid tert-butyl ester

HRID 1512038Notes

Reaction equation

HRID 1512038 reaction equation
[Cl:1][C:2]1[CH:9]=[C:6]([CH:7]=[O:8])[C:5]([OH:10])=[CH:4][CH:3]=1.[C:11]([O:15][C:16](=[O:21])[C:17](Br)([CH3:19])[CH3:18])([CH3:14])([CH3:13])[CH3:12].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C)C=O>[C:11]([O:15][C:16](=[O:21])[C:17]([O:10][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:9][C:6]=1[CH:7]=[O:8])([CH3:19])[CH3:18])([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 124815-Chloro-salicylaldehydeHCID 90290tert-Butyl 2-bromo-2-methylpropionate

Product 1

HCID 575662212-(4-Chloro-2-formyl-phenoxy)-2-methyl-propionic acid tert-butyl esterYield 54.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of 5-chlorosalicylaldehyde (5 g, 32 mmol) in N,N-dimethylformamide (100 mL) was added 2-bromo-2-methyl-propionic acid tert-butyl ester (10.7 g, 48 mmol), Cs2CO3 (3.1 g, 95 mmol). The reaction mixture was heated at 140° C. for 18 h. The mixture was partitioned between ethyl acetate and water. The organic layer was separated, and aqueous layer was extracted with ethyl acetate. The organic layers were combined, washed with water, brine, dried over Na2SO4 and concentrated to give 2-(4-chloro-2-formyl-phenoxy)-2-methyl-propionic acid tert-butyl ester as a pale yellow solid (Yield 5.2 g, 54%)

Workup

  1. customThe mixture was partitioned between ethyl acetate and water
  2. customThe organic layer was separated
  3. extractionaqueous layer was extracted with ethyl acetate
  4. washwashed with water, brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0055460bcd0648c187ffb07034b7625b
Source dataset
uspto-grants-2012_07
Patent number
US08217051B2

Reaction notes

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