2-Chloro-4-fluorobenzoic acid → 5-((2,2,2-Trifluoroacetamido)methyl)-2-chloro-4-fluorobenzoic acid

HRID 59359

Reaction equation

HRID 59359 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[F:12][C:13]([F:20])([F:19])[C:14]([NH:16][CH2:17]O)=[O:15]>OS(O)(=O)=O>[F:12][C:13]([F:20])([F:19])[C:14]([NH:16][CH2:17][C:8]1[C:9]([F:11])=[CH:10][C:2]([Cl:1])=[C:3]([CH:7]=1)[C:4]([OH:6])=[O:5])=[O:15]

Participants

4

Reactant 2

HCID 752592-Chloro-4-fluorobenzoic acidHCID 30849312,2,2-Trifluoro-N-(hydroxymethyl)acetamide

Product 1

HCID 897366685-((2,2,2-Trifluoroacetamido)methyl)-2-chloro-4-fluorobenzoic acidYield 667,543%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

The title compound was prepared according to the procedure described in step-1 of Intermediate-26 by using 2-chloro-4-fluorobenzoic acid (5.0 g, 0.002 mmol), 2,2,2-trifluoro-N-(hydroxymethyl)acetamide (4.0 g, 0.002 mmol) and conc. H2SO4 (50 mL) to afford 4.0 g of the desired product. 1H NMR (400 MHz, DMSO d6): δ 4.44 (d, J=12.0 Hz, 2H), 7.59 (m, 1H), 7.92 (m, 1H), 10.0 (br s, 1H), 13.5 (br s, 1H).

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-ad3c3e64c52a49f889c04540331e0030
Source dataset
uspto-grants-2016_09
Patent number
US09439890B2

Linked notes

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