5-Amino-2-nitrobenzoic acid → 2-Nitro-5-(2,3,5,6-tetrafluoro-4-trifluoromethylbenzylamino)benzoic acid

HRID 458259Notes

Reaction equation

HRID 458259 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[F:14][C:15]1[C:22]([F:23])=[C:21]([C:24]([F:27])([F:26])[F:25])[C:20]([F:28])=[C:19]([F:29])[C:16]=1[CH2:17]Br>>[N+:11]([C:5]1[CH:4]=[CH:3][C:2]([NH:1][CH2:17][C:16]2[C:19]([F:29])=[C:20]([F:28])[C:21]([C:24]([F:25])([F:27])[F:26])=[C:22]([F:23])[C:15]=2[F:14])=[CH:10][C:6]=1[C:7]([OH:9])=[O:8])([O-:13])=[O:12]

Participants

3

Reactant 2

HCID 832985-Amino-2-nitrobenzoic acidHCID 1271374-(Trifluoromethyl)-2,3,5,6-tetrafluorobenzyl bromide

Product 1

HCID 102510932-Nitro-5-(2,3,5,6-tetrafluoro-4-trifluoromethylbenzylamino)benzoic acidYield 76.3%

Procedure

According to the similar procedure in Synthesis Example 1, by using 5-amino-2-nitrobenzoic acid (1.03 g, 5.65 mmole) and 2,3,5,6-tetrafluoro-4-trifloromethylbenzyl bromide (1.01 g, 6.04 mmole)(ACROS, 33074-0010), 1.50 g (76.3% yield) of 2-nitro-5-(2,3,5,6-tetrafluoro-4-trifluoromethylbenzylamino)benzoic acid was obtained as a pale yellow solid.

Workup

  1. customAccording to the similar procedure in Synthesis Example 1

Sources & evidence

ORD record
ord-4734dbec2c9d40588fbfa710da54e6f9
Source dataset
uspto-grants-2007_03
Patent number
US07189878B2

Reaction notes

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