Potassium Carbonate → 2-(4-Chloro-5-fluoro-2-formyl-phenoxy)-2-methyl-propionic acid methyl ester

HRID 658944Notes

Reaction equation

HRID 658944 reaction equation
[Cl:1][C:2]1[C:3]([F:11])=[CH:4][C:5]([OH:10])=[C:6]([CH:9]=1)[CH:7]=[O:8].[CH3:12][O:13][C:14](=[O:19])[C:15](Br)([CH3:17])[CH3:16].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:12][O:13][C:14](=[O:19])[C:15]([O:10][C:5]1[CH:4]=[C:3]([F:11])[C:2]([Cl:1])=[CH:9][C:6]=1[CH:7]=[O:8])([CH3:17])[CH3:16]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 90097Methyl 2-bromo-2-methylpropionateHCID 71721325-Chloro-4-fluoro-2-hydroxybenzaldehyde

Product 1

HCID 595493062-(4-Chloro-5-fluoro-2-formyl-phenoxy)-2-methyl-propionic acid methyl esterYield 85.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 5-chloro-4-fluoro-2-hydroxy-benzaldehyde (0.8 g, 4.6 mmol), 2-bromo-2-methyl-propionic acid methyl ester (1.6 g, 9.2 mmol) and K2CO3 (2 g, 14.5 mmol) in DMF (40 mL) was placed in a sealed tube and heated by irradiation in microwave reactor at 140° C. for 12 min. After cooled to room temperature, the mixture was partitioned between EtOAc and water. The organic layer was separated, washed with water, dried over anhydrous Na2SO4 and concentrated to give the thitle compound as a brown solid (1.08 g).

Workup

  1. customwas placed in a sealed tube
  2. temperatureAfter cooled to room temperature
  3. customthe mixture was partitioned between EtOAc and water
  4. customThe organic layer was separated
  5. washwashed with water
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-5ebe632a002149bdbfb6092a30ca81ee
Source dataset
uspto-grants-2011_12
Patent number
US08076482B2

Reaction notes

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