Water → HCID 89580615, compound

HRID 1500978Notes

Reaction equation

HRID 1500978 reaction equation
F[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH3:12].[Br:13][C:14]1[C:19]([CH2:20][CH3:21])=[CH:18][CH:17]=[CH:16][C:15]=1[OH:22].C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[Br:13][C:14]1[C:19]([CH2:20][CH3:21])=[CH:18][CH:17]=[CH:16][C:15]=1[O:22][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 18788764Methyl 4-fluoro-3-methylbenzoateHCID 18947832HCID 18947832, compound

Product 1

HCID 89580615HCID 89580615, compoundYield 60.1%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
130 °C

Procedure

To a solution of methyl 4-fluoro-3-methylbenzoate (1.7 g, 10 mmol) and 2-bromo-3-ethylphenol (2.0 g, 10 mmol) in dimethyl sulfoxide (10 mL) was added potassium carbonate (2.8 g, 20 mmol). The reaction mixture was stirred at 130° C. for 3 hours. After the reaction, the mixture was poured into water (50 mL) and the solution was extracted with ethyl acetate (50 mL), washed with water (50 mL). The organic phase was dried over anhydrous sodium sulfate. The mixture was filtered and the solvent was removed under reduced pressure to give the pure product methyl 4-(2-bromo-3-ethylphenoxy)-3-methylbenzoate as colorless oil (2.10 g, 60%).

Workup

  1. customAfter the reaction
  2. extractionthe solution was extracted with ethyl acetate (50 mL)
  3. washwashed with water (50 mL)
  4. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  5. filtrationThe mixture was filtered
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-00a18056c7aa4985bdc28dfae4d87d58
Source dataset
uspto-grants-2015_12
Patent number
US09206128B2

Reaction notes

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