4-(Trifluoromethyl)-2,3,5,6-tetrafluorobenzyl bromide → 5-(2,3,5,6-Tetrafluoro-4-trifluoromethylbenzylamino)-2-trifluoromethoxybenzoic acid

HRID 2222769Notes

Reaction equation

HRID 2222769 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][C:12]([F:15])([F:14])[F:13])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[F:16][C:17]1[C:24]([F:25])=[C:23]([C:26]([F:29])([F:28])[F:27])[C:22]([F:30])=[C:21]([F:31])[C:18]=1[CH2:19]Br>CN(C=O)C>[F:16][C:17]1[C:24]([F:25])=[C:23]([C:26]([F:29])([F:27])[F:28])[C:22]([F:30])=[C:21]([F:31])[C:18]=1[CH2:19][NH:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][C:12]([F:13])([F:14])[F:15])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 1271374-(Trifluoromethyl)-2,3,5,6-tetrafluorobenzyl bromideHCID 118309945-amino-2-(trifluoromethoxy)benzoic Acid

Product 1

HCID 100494665-(2,3,5,6-Tetrafluoro-4-trifluoromethylbenzylamino)-2-trifluoromethoxybenzoic acidYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

According to the similar procedure in Synthesis Example 1, by using 5-amino-2-trifluoromethoxybenzoic acid (1.35 g, 6.23 mmole), DMF (50 ml), TEA (6 ml), and 2,3,5,6-tetrafluoro-4-trifluoromethylbenzyl bromide (1.10 ml, 6.7.3 mmole), 2.25 g (81.0% yield) of 5-(2,3,5,6-tetrafluoro-4-trifluoromethylbenzylamino)-2-trifluoromethoxybenzoic acid was obtained as a yellow solid.

Workup

  1. customAccording to the similar procedure in Synthesis Example 1

Sources & evidence

ORD record
ord-9f1ff4bc70c0477c96e93bfd3e410121
Source dataset
uspto-grants-2008_05
Patent number
US07371896B2

Reaction notes

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