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

HRID 2251697Notes

Reaction equation

HRID 2251697 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[F:13][C:14]1[C:21]([F:22])=[C:20]([C:23]([F:26])([F:25])[F:24])[C:19]([F:27])=[C:18]([F:28])[C:15]=1[CH2:16]Br>CN(C=O)C>[CH3:12][O:11][C:5]1[CH:4]=[CH:3][C:2]([NH:1][CH2:16][C:15]2[C:18]([F:28])=[C:19]([F:27])[C:20]([C:23]([F:24])([F:26])[F:25])=[C:21]([F:22])[C:14]=2[F:13])=[CH:10][C:6]=1[C:7]([OH:9])=[O:8]

Participants

4

Reactant 2

HCID 1271374-(Trifluoromethyl)-2,3,5,6-tetrafluorobenzyl bromideHCID 135492445-Amino-2-methoxybenzoic acid

Product 1

HCID 100463322-Methoxy-5-(2,3,5,6-tetrafluoro-4-trifluoromethylbenzylamino)benzoic acidYield 31.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

According to the similar procedure in Synthesis Example 1, by using 5-amino-2-methoxy-benzoic acid (2.10 g, 12.7 mmole), DMF (50 ml), TEA (6 ml), and 2,3,5,6-tetrafluoro-4-trifluoromethylbenzyl bromide (2.00 ml, 14.0 mmole), 1.50 g (31.5% yield) of 2-methoxy-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-ef57b55275d1455c804bf00d3825e0ff
Source dataset
uspto-grants-2008_01
Patent number
US07319160B2

Reaction notes

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