4-(Trifluoromethyl)-2,3,5,6-tetrafluorobenzyl bromide → 2-Methyl-5-(2,3,5,6-tetrafluoro-4-trifluoromethylbenzylamino)benzoic acid

HRID 2222767Notes

Reaction equation

HRID 2222767 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[F:12][C:13]1[C:20]([F:21])=[C:19]([C:22]([F:25])([F:24])[F:23])[C:18]([F:26])=[C:17]([F:27])[C:14]=1[CH2:15]Br>CN(C=O)C>[CH3:11][C:5]1[CH:4]=[CH:3][C:2]([NH:1][CH2:15][C:14]2[C:17]([F:27])=[C:18]([F:26])[C:19]([C:22]([F:23])([F:25])[F:24])=[C:20]([F:21])[C:13]=2[F:12])=[CH:10][C:6]=1[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 1271374-(Trifluoromethyl)-2,3,5,6-tetrafluorobenzyl bromideHCID 103746145-Amino-2-methylbenzoic acid

Product 1

HCID 103397872-Methyl-5-(2,3,5,6-tetrafluoro-4-trifluoromethylbenzylamino)benzoic acidYield 27%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

According to the similar procedure in Synthesis Example 1, by using 5-amino-2-methylbenzoic acid (2.06 g 15.0 mmole), DMF (60 ml), TEA (4 ml), and 2,3,5,6-tetrafluoro-4-trifluoromethylbenzyl bromide (5.52 ml, 17.7 mmole), 1.50 g (27.0% yield) of 2-methyl-5-(2,3,5,6-tetrafluoro-4-trifluoromethylbenzylamino)benzoic acid was obtained as a yellow solid.

Workup

  1. customAccording to the similar procedure in Synthesis Example 1

Sources & evidence

ORD record
ord-94e3e38246fd4c14bc0f3c585c8c722c
Source dataset
uspto-grants-2008_05
Patent number
US07371896B2

Reaction notes

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