Water → 2-Chloro-3-ethyl-4-fluorobenzoic acid

HRID 2046638Notes

Reaction equation

HRID 2046638 reaction equation
BrBr.[OH-:3].[Na+].[Cl:5][C:6]1[C:11]([CH2:12][CH3:13])=[C:10]([F:14])[CH:9]=[CH:8][C:7]=1[C:15](=[O:17])C.O>O1CCOCC1>[Cl:5][C:6]1[C:11]([CH2:12][CH3:13])=[C:10]([F:14])[CH:9]=[CH:8][C:7]=1[C:15]([OH:17])=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 24408BromineHCID 593705071-(2-Chloro-3-ethyl-4-fluorophenyl)ethanone

Product 1

HCID 593705272-Chloro-3-ethyl-4-fluorobenzoic acidYield 88.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
10 °C

Procedure

Bromine (8.94 g) was added to an aqueous solution (35.6 mL) of sodium hydroxide (7.61 g) with stirring at 10° C., and a solution (37.4 mL) of 1-(2-chloro-3-ethyl-4-fluorophenyl)ethanone (3.74 g) in dioxane was added under ice-cooling (sodium chloride-ice bath). The mixture was warmed to room temperature and, after stirring for 1 hr, poured into water and partitioned with chloroform. The aqueous layer was adjusted to pH=3 with concentrated hydrochloric acid, and extracted with ether. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated to give the title compound as colorless crystals (yield: 3.33 g).

Workup

  1. temperatureThe mixture was warmed to room temperature
  2. stirringafter stirring for 1 hr
  3. custompartitioned with chloroform
  4. extractionextracted with ether
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b5df6113123f4577989edafcc8898a18
Source dataset
uspto-grants-2013_11
Patent number
US08592452B2

Reaction notes

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