2-Chlorobenzoic Acid → 2-Chloro-5-[(trifluoroacetamido)methyl]benzoic acid

HRID 59267

Reaction equation

HRID 59267 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[F:11][C:12]([F:19])([F:18])[C:13]([NH:15][CH2:16]O)=[O:14]>OS(O)(=O)=O>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([CH2:16][NH:15][C:13](=[O:14])[C:12]([F:19])([F:18])[F:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 83742-Chlorobenzoic AcidHCID 30849312,2,2-Trifluoro-N-(hydroxymethyl)acetamide

Product 1

HCID 584832772-Chloro-5-[(trifluoroacetamido)methyl]benzoic acidYield 81.4%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To a solution of 2-chlorobenzoic acid (0.500 g, 3.49 mmol) in conc. H2SO4 was added 2,2,2-trifluoro-N-(hydroxymethyl)acetamide (0.547 g, 3.49 mmol). The mixture was stirred at RT for 16 h. The reaction mixture was poured into ice-water and stirred for 2 h. The precipitate obtained was collected by filtration, dried and re-crystallized from toluene/butan-2-one (7:1) to afford 0.800 g of the title product. 1H NMR (300 MHz, DMSO d6): δ 4.42 (d, J=6.0 Hz, 2H), 7.43 (d, J=9.9 Hz, 1H), 7.54 (d, J=8.4 Hz, 1H), 7.71 (s, 1H), 10.06 (br s, 1H), 13.47 (br s, 1H); MS (m/z): 280.18 (M−H)−.

Workup

  1. stirringstirred for 2 h
  2. customThe precipitate obtained
  3. filtrationwas collected by filtration
  4. customdried
  5. customre-crystallized from toluene/butan-2-one (7:1)

Sources & evidence

ORD record
ord-5463cdfd29bf4b898a6ed7d0e567629d
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Linked notes

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