Water → HCID 66666627, compound

HRID 1620342Notes

Reaction equation

HRID 1620342 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8](F)=[C:7]([Br:12])[CH:6]=1)=[O:4].[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1.CC(C)([O-])C.[K+].O>CS(C)=O>[Br:12][C:7]1[CH:6]=[C:5]([CH:10]=[CH:9][C:8]=1[O:20][C:17]1[CH:18]=[CH:19][C:14]([Cl:13])=[CH:15][CH:16]=1)[C:3]([OH:2])=[O:4].[CH3:1][O:2][C:3](=[O:4])[C:5]1[CH:10]=[CH:9][C:8]([O:20][C:17]2[CH:18]=[CH:19][C:14]([Cl:13])=[CH:15][CH:16]=2)=[C:7]([Br:12])[CH:6]=1

Participants

7

Reactant 4

HCID 962WaterHCID 46844-ChlorophenolHCID 7018022Methyl 3-bromo-4-fluorobenzoateHCID 23665647Potassium tert-butoxide

Product 2

HCID 66666627HCID 66666627, compoundHCID 66667416HCID 66667416, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of methyl-3-bromo-4-fluoro benzoate (20 g, 86 mmol) and 4-chlorophenol (11.0 g, 171 mmol) in dimethylsulfoxide (500 mL) was added potassium tert-butoxide (19.3 g, 171 mmol) and the reaction mixture was stirred at 120° C. for 16 hours and then poured into 500 mL of water and extracted with dichloromethane (3×100 mL). The combined extracts were dried over anhydrous sodium sulfate, filtered and evaporated in vacuo. The residue was purified via column chromatography on silica gel (1:1 petroleum ether:EtOAc) to yield 18 g (55 mmol) of 3-bromo-4-(4-chlorophenoxy)-benzoic acid and 2 g of the title compound.

Workup

  1. extractionextracted with dichloromethane (3×100 mL)
  2. dry with materialThe combined extracts were dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe residue was purified via column chromatography on silica gel (1:1 petroleum ether:EtOAc)

Sources & evidence

ORD record
ord-e9d18cac07f443ea9680d8d930f8a3ea
Source dataset
uspto-grants-2014_07
Patent number
US08772343B2

Reaction notes

Loading…