Hydrochloric Acid → (3-Fluoro-2-nitrophenyl)acetic acid

HRID 469350Notes

Reaction equation

HRID 469350 reaction equation
[F:1][C:2]1[C:3]([N+:17]([O-:19])=[O:18])=[C:4]([CH:8](C(OC)=O)[C:9]([O:11]C)=[O:10])[CH:5]=[CH:6][CH:7]=1.Cl>O>[F:1][C:2]1[C:3]([N+:17]([O-:19])=[O:18])=[C:4]([CH2:8][C:9]([OH:11])=[O:10])[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 24824212Dimethyl (3-fluoro-2-nitrophenyl)propanedioate

Product 1

HCID 24824213(3-Fluoro-2-nitrophenyl)acetic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

28.0 g (103 mmol) dimethyl 2-(3-fluoro-2-nitro-phenyl)-malonate were added to 120 mL water and 120 mL conc. hydrochloric acid and refluxed for 5 h. The mixture was cooled to RT and extracted several times with EtOAc. The combined organic phases were dried on magnesium sulphate, filtered and evaporated down i. vac. The residue was triturated with PE/EtOAc=3/1 and suction filtered.

Workup

  1. temperaturerefluxed for 5 h
  2. extractionextracted several times with EtOAc
  3. customThe combined organic phases were dried on magnesium sulphate
  4. filtrationfiltered
  5. customevaporated down i
  6. customThe residue was triturated with PE/EtOAc=3/1 and suction
  7. filtrationfiltered

Sources & evidence

ORD record
ord-2792941a0cc745de8ff6627a1b1408a9
Source dataset
uspto-grants-2014_01
Patent number
US08629137B2

Reaction notes

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