Chlorosuccinimide → 5-Chloro-2-ethoxybenzoic acid

HRID 78477

Reaction equation

HRID 78477 reaction equation
[CH2:1]([O:3][C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])[CH3:2].[Cl:13]N1C(=O)CCC1=O>C(#N)C>[Cl:13][C:10]1[CH:11]=[CH:12][C:4]([O:3][CH2:1][CH3:2])=[C:5]([CH:9]=1)[C:6]([OH:8])=[O:7]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 672522-Ethoxybenzoic acid

Product 1

HCID 50985705-Chloro-2-ethoxybenzoic acid

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 2-ethoxybenzoic acid (4.4 g, 26.6 mmol) in 80 mL of acetonitrile at 0° C. was added N-chlorosuccinimide (3.7 g, 28 mmol) in 20 mL of acetonitrile dropwise over 30 minutes. The reaction mixture was warmed to ambient temperature and the mixture was allowed to stir for 70 hours. The mixture was quenched with 20 mL of H2O and the layers were separated. The aqueous layer was extracted with three 15 mL portions of CH2Cl2 and the combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. Purification via recrystallization with ether and hexanes afforded the title compound. MS (DCI/NH3) m/z 201 (M+H)+, 218 (M+NH4)+.

Workup

  1. customThe mixture was quenched with 20 mL of H2O
  2. customthe layers were separated
  3. extractionThe aqueous layer was extracted with three 15 mL portions of CH2Cl2
  4. dry with materialthe combined organic extracts were dried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification
  8. customvia recrystallization with ether and hexanes

Sources & evidence

ORD record
ord-029cf09010894e74b3ccb96a99e26c5d
Source dataset
uspto-grants-2014_09
Patent number
US08841334B2

Linked notes

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