2,4-Difluoronitrobenzene → Ethyl 6-bromo-2-(5-fluoro-2-nitroanilino)benzo[b]thiophene-3-carboxylate

HRID 649907Notes

Reaction equation

HRID 649907 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:8]([NH2:15])[S:7][C:6]=2[CH:16]=1.F[C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=1[N+:25]([O-:27])=[O:26]>CS(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])=[C:8]([NH:15][C:18]3[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=3[N+:25]([O-:27])=[O:26])[S:7][C:6]=2[CH:16]=1

Participants

4

Reactant 2

HCID 679672,4-DifluoronitrobenzeneHCID 18422163Ethyl 6-bromo-2-aminobenzo[b]thiophene-3-carboxylate

Product 1

HCID 18422148Ethyl 6-bromo-2-(5-fluoro-2-nitroanilino)benzo[b]thiophene-3-carboxylateYield 77.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

In the same manner as in Starting Material Synthesis Example 4 and using ethyl 6-bromo-2-aminobenzo[b]thiophene-3-carboxylate (8.8 g), 2,4-difluoronitrobenzene (5.6 g) and dimethyl sulfoxide (100 ml), ethyl 6-bromo-2-(5-fluoro-2-nitroanilino)benzo[b]thiophene-3-carboxylate (10 g) was obtained.

Workup

  1. customMaterial Synthesis Example 4

Sources & evidence

ORD record
ord-9af5125668ec4ac58507b58c180803fd
Source dataset
uspto-grants-2001_08
Patent number
US06271225B1

Reaction notes

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