4-(Trifluoromethyl)-2,3,5,6-tetrafluorobenzyl bromide → HCID 10455841, compound

HRID 2251706Notes

Reaction equation

HRID 2251706 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][C:12](=[O:15])[CH2:13][CH3:14])=[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>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C>[C:12]([O:11][C:5]1[CH:4]=[CH:3][C:2]([NH:1][CH2:19][C:18]2[C:21]([F:31])=[C:22]([F:30])[C:23]([C:26]([F:27])([F:29])[F:28])=[C:24]([F:25])[C:17]=2[F:16])=[CH:10][C:6]=1[C:7]([OH:9])=[O:8])(=[O:15])[CH2:13][CH3:14]

Participants

5

Reactant 2

HCID 1271374-(Trifluoromethyl)-2,3,5,6-tetrafluorobenzyl bromideHCID 22341900HCID 22341900, compound

Product 1

HCID 10455841HCID 10455841, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

According to the similar procedure in Synthesis Example 14-4, by using 5-amino-2-propanoyloxybenzoic acid (0.32 g, 1.53 mmole) which was prepared from Synthesis Example (15-2), DMF (10 ml), TEA (0.05 ml), tetrabutyl ammonium iodide (3 mg), and 2,3,5,6-tetrafluoro-4-trifluoromethylbenzyl bromide (0.38 ml, 2.30 mmole), 0.34 g (51.0% yield) of was obtained 2-propanoyloxy-5-(2,3,5,6-tetrafluoro-4-trifluoromethylbenzylamino)benzoic acid as a white solid.

Workup

  1. customAccording to the similar procedure in Synthesis Example 14-4

Sources & evidence

ORD record
ord-83ab02be42f24ba19306b9496a91ab99
Source dataset
uspto-grants-2008_01
Patent number
US07319160B2

Reaction notes

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