Trifluoroacetic acid → 2-(3,5-Difluoro-4-nitrophenyl)acetic acid

HRID 1050915Notes

Reaction equation

HRID 1050915 reaction equation
FC(F)(F)C(O)=O.[F:8][C:9]1[CH:10]=[C:11]([CH2:19][C:20]([O:22]C(C)(C)C)=[O:21])[CH:12]=[C:13]([F:18])[C:14]=1[N+:15]([O-:17])=[O:16]>C(Cl)Cl>[F:8][C:9]1[CH:10]=[C:11]([CH2:19][C:20]([OH:22])=[O:21])[CH:12]=[C:13]([F:18])[C:14]=1[N+:15]([O-:17])=[O:16]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18188101t-Butyl 3,5-difluoro4-nitrophenylacetate

Product 1

HCID 179671372-(3,5-Difluoro-4-nitrophenyl)acetic acidYield 80.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (150 mL) was added dropwise over 20 minutes to a cold (0° C.) solution of tert-butyl (3,5-difluoro-4-nitrophenyl)acetate (83.33 g, 305 mmol) in DCM (300 mL). On completion of the addition, the reaction mixture was allowed to warm to room temperature and stirred for 3 hours. The reaction mixture was concentrated under reduced pressure to leave a sticky brown solid. Trituration with heptanes afforded the title compound as a yellow solid (53.29 g, 67% yield over two steps).

Workup

  1. additionOn completion of the addition
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customto leave a sticky brown solid

Sources & evidence

ORD record
ord-0ec6a68eadb341788bdfb25e50befbb9
Source dataset
uspto-grants-2016_07
Patent number
US09388136B2

Reaction notes

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