Water → HCID 67508817, compound

HRID 623488Notes

Reaction equation

HRID 623488 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][C:10]1[C:11]([O:20][CH2:21][C:22]([F:25])([F:24])[F:23])=[N:12][CH:13]=[C:14]([CH:19]=1)[C:15]([O:17][CH3:18])=[O:16].O>ClC(Cl)C.N(C(C)(C)C#N)=NC(C)(C)C#N>[Br:1][CH2:9][C:10]1[C:11]([O:20][CH2:21][C:22]([F:25])([F:23])[F:24])=[N:12][CH:13]=[C:14]([CH:19]=1)[C:15]([O:17][CH3:18])=[O:16]

Participants

6

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 67508999HCID 67508999, compound

Product 1

HCID 67508817HCID 67508817, compoundYield 99.8%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 63651,1-DichloroethaneSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of N-bromosuccinimide (464 mg, 2.61 mmol), 2,2′-azobis(2-methylpropionitrile) (16 mg, 0.10 mmol) and methyl 5-methyl-6-(2,2,2-trifluoroethoxy)nicotinate (500 mg, 2.01 mmol, Step-1) in dichloroethane (10 mL) is stirred at 85° C. for 4 hours. After cooling to room temperature, the reaction mixture is poured into water extracted with dichloroethane and dried over sodium sulfate and concentrated in vacuo. The residue is purified by column chromatography on silica gel eluting with n-Hexane/ethyl acetate (10:1) to give 658 mg (>99% yield) of the title compound as colorless oil.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with dichloroethane
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by column chromatography on silica gel eluting with n-Hexane/ethyl acetate (10:1)

Sources & evidence

ORD record
ord-d3e3272dcc634548824243b90d25de04
Source dataset
uspto-grants-2016_04
Patent number
US09302991B2

Reaction notes

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