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

HRID 1469717Notes

Reaction equation

HRID 1469717 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].OS(O)(=O)=O.[F:16][C:17]([F:24])([F:23])[C:18]([NH:20][CH2:21]O)=[O:19]>>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([CH2:21][NH:20][C:18](=[O:19])[C:17]([F:24])([F:23])[F:16])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 83742-Chlorobenzoic AcidHCID 30849312,2,2-Trifluoro-N-(hydroxymethyl)acetamide

Product 1

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

Procedure

To a solution of 2-chlorobenzoic acid (500 mg, 3.49 mmol) in cone. H2SO4 was added 2,2,2-trifluoro-N-(hydroxymethyl)acetamide (547 mg, 3.49 mmol). The mixture was stirred at rt for 16 h. The reaction mixture was poured into ice-water and the precipitate obtained, was collected by filtration, dried and the re-crystallized from toluene/butan-2-one (7:1) to afford 800 mg of the title product. 1H NMR (300 MHz, DMSO d6): δ 13.47 (br s, 1H), 10.06 (br s, 1H), 7.71 (s, 1H), 7.54 (d, J=8.4 Hz, 1H), 7.43 (d, J=9.9 Hz, 1H), 4.42 (d, J=6.0 Hz, 2H); MS (m/z): 280.18 (M−H)−.

Workup

  1. customthe precipitate obtained
  2. filtrationwas collected by filtration
  3. customdried
  4. customthe re-crystallized from toluene/butan-2-one (7:1)

Sources & evidence

ORD record
ord-ec2f473abc944adeaf7ba544e8f6ccc5
Source dataset
uspto-grants-2015_04
Patent number
US09006257B2

Reaction notes

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