Water → 1-(4,4,4-Trifluorobutyl)-6-bromo-benzo[cd]indol-2(1h)-one

HRID 433097Notes

Reaction equation

HRID 433097 reaction equation
[Br:1][C:2]1[C:3]2[C:4]3[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]=3[CH:12]=[CH:13][CH:14]=2.C([O-])([O-])=O.[K+].[K+].[F:21][C:22]([F:28])([F:27])[CH2:23][CH2:24][CH2:25]I.O>CN(C)C=O>[Br:1][C:2]1[C:3]2[C:4]3[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:25][CH2:24][CH2:23][C:22]([F:28])([F:27])[F:21])[C:6](=[O:11])[C:5]=3[CH:12]=[CH:13][CH:14]=2

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 7547635-Bromo-8-naphtholactamHCID 27751891,1,1-Trifluoro-4-iodobutane

Product 1

HCID 187579401-(4,4,4-Trifluorobutyl)-6-bromo-benzo[cd]indol-2(1h)-oneYield 85.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a solutiion of 6-bromo-benzo[cd]indol-2(1H)-one (1 g, 4 mmol) in N,N-dimethyl formamide was added K2CO3 (5.53 g, 40 mmol) and the resulting mixture was stirred for 0.5 hour under nitrogen. 4,4,4-trifluorobutyl iodide (915 mg, 4 mmol ) was next injected to the solution and the mixture was heated at 60° C. for 18 hours. The reaction media was next poured into 200 ml water and extracted with trichloromethane (3×100 ml). Column chromatography using gradient ethyl acetate in hexane (10˜20%) gave the desired product (1.225 g, 85%).

Workup

  1. customThe reaction media
  2. extractionextracted with trichloromethane (3×100 ml)

Sources & evidence

ORD record
ord-304023f8ba8d4a27b8bbd5781f6360cb
Source dataset
uspto-grants-2003_12
Patent number
US06667303B1

Reaction notes

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