Bromine → HCID 15335328, compound

HRID 1449629Notes

Reaction equation

HRID 1449629 reaction equation
[C:1]([C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4]=1[C:12]([F:15])([F:14])[F:13])#[N:2].[Br:16]Br>C(O)(=O)C>[Br:16][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[NH:5][C:4]([C:12]([F:15])([F:13])[F:14])=[C:3]2[C:1]#[N:2]

Participants

4

Reactant 2

HCID 24408BromineHCID 15335327HCID 15335327, compound

Product 1

HCID 15335328HCID 15335328, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3-cyano-2-(trifluoromethyl)indole (1.05 g, 5.0 mmole) in acetic acid is treated with Br2 (0.6 mL, 6.0 mmole) at room temperature, and stirred until reaction is complete by TLC. The reaction mixture is worked up as described in Example 22 to afford the title product as a white solid after chromatography (silica gel and 4:1 hexanes:ethyl acetate) and crystallization, 0.95 g (65% yield), mp 188°-191.5° C., identified by IR, 1HNMR, 19FNMR and mass spectral analyses.

Sources & evidence

ORD record
ord-b67787c6847d42dca38409597ec60f0f
Source dataset
uspto-grants-1997_02
Patent number
US05599832

Reaction notes

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