4-(Trifluoromethyl)-2,3,5,6-tetrafluorobenzyl bromide → HCID 10028645, compound

HRID 584873Notes

Reaction equation

HRID 584873 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][C:12]([CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)=[O:13])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[F:20][C:21]1[C:28]([F:29])=[C:27]([C:30]([F:33])([F:32])[F:31])[C:26]([F:34])=[C:25]([F:35])[C:22]=1[CH2:23]Br>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C>[CH:14]1([C:12]([O:11][C:5]2[CH:4]=[CH:3][C:2]([NH:1][CH2:23][C:22]3[C:25]([F:35])=[C:26]([F:34])[C:27]([C:30]([F:31])([F:33])[F:32])=[C:28]([F:29])[C:21]=3[F:20])=[CH:10][C:6]=2[C:7]([OH:9])=[O:8])=[O:13])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 2

HCID 1271374-(Trifluoromethyl)-2,3,5,6-tetrafluorobenzyl bromideHCID 22341904HCID 22341904, compound

Product 1

HCID 10028645HCID 10028645, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

According to the similar procedure in Synthesis Example (14-4), by using 5-amino-2-cyclohexanecarbonyloxybenzoic acid (1.03 g, 3.95 mmole) which was prepared from Synthesis Example (16-2), DMF (15 ml), TEA (0.10 ml), tetrabutyl ammonium iodide (10 mg), and 2,3,5,6-tetrafluoro-4-trifluoromethylbenzyl bromide (1.01 ml, 5.92 mmole), 0.95 g (49.0% yield) of was obtained 2-cyclohexanecarbonyloxy-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-f815442b41f648ebaed4ea77b6178e23
Source dataset
uspto-grants-2005_08
Patent number
US06927303B2

Reaction notes

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