1-Chloro-2-nitrobenzene → N-(4-chloro-3-nitrobenzyl)-2,2,2-trifluoroacetamide

HRID 59289

Reaction equation

HRID 59289 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9].O[CH2:12][NH:13][C:14](=[O:19])[C:15]([F:18])([F:17])[F:16]>S(=O)(=O)(O)O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:12][NH:13][C:14](=[O:19])[C:15]([F:18])([F:17])[F:16])=[CH:4][C:3]=1[N+:8]([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 69451-Chloro-2-nitrobenzeneHCID 30849312,2,2-Trifluoro-N-(hydroxymethyl)acetamide

Product 1

HCID 19879857N-(4-chloro-3-nitrobenzyl)-2,2,2-trifluoroacetamideYield 30,891.9%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of 1-chloro-2-nitrobenzene (10.0 g, 0.063 mmol) in conc. sulphuric acid (150 mL) was added N-hydroxy methyl trifluoro acetamide (9.98 g, 0.069 mmol). The reaction mixture was heated at 70-80° C. for 24 h. The reaction mass was quenched in ice cold water, neutralised with sodium hydroxide and extracted with DCM. The organic layer was concentrated and the obtained crude product was purified by column chromatography on silica gel eluting with 4% EtOAc: pet. ether to afford 5.5 g of desired product. 1H NMR (300 MHz, DMSO d6): 4.48 (d, J=3.9 Hz, 2H), 7.62-7.64 (m, 1H), 7.72-7.78 (m, 1H), 7.97-8.01 (m, 1H), 10.09 (brs, 1H).

Workup

  1. customThe reaction mass was quenched in ice cold water
  2. extractionextracted with DCM
  3. concentrationThe organic layer was concentrated
  4. customthe obtained crude product
  5. customwas purified by column chromatography on silica gel eluting with 4% EtOAc

Sources & evidence

ORD record
ord-d0adaacf7d1f472794d4e88810d0c6df
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Linked notes

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