N-bromobutanimide → HCID 14129197, compound

HRID 1776034Notes

Reaction equation

HRID 1776034 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:6]([O:9][C:10]([F:13])([F:12])[F:11])=[CH:5][C:3]=1[NH2:4].[Br:14]N1C(=O)CCC1=O>CN(C=O)C>[Br:14][C:7]1[C:6]([O:9][C:10]([F:11])([F:12])[F:13])=[CH:5][C:3]([NH2:4])=[C:2]([F:1])[CH:8]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 144393082-Fluoro-5-(trifluoromethoxy)aniline

Product 1

HCID 14129197HCID 14129197, compoundYield 59.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a mixture of 2-fluoro-5-(trifluoromethoxy)aniline (1 g, 5 mmol) dissolved in DMF (2 mL) was slowly added a solution of N-bromosuccinimide (1.1 g, 6.2 mmol) dissolved in DMF (2 mL). The reaction mixture was stirred at room temperature for 1 h, concentrated and extracted with ethyl acetate/water. The organic layer was dried over sodium sulfate, filtered, concentrated and purified by silica gel chromatography (eluted 0-10% ethyl acetate:hexanes) to produce the title intermediate as a red oil (818 mg, 58% yield). (m/z): [M+H]+ calcd for C7H4BrF4NO 273.94, 275.94. found 276.1.

Workup

  1. concentrationconcentrated
  2. extractionextracted with ethyl acetate/water
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by silica gel chromatography (eluted 0-10% ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-391804f8c90b4613a52c0dc62c8d1850
Source dataset
uspto-grants-2016_02
Patent number
US09260414B2

Reaction notes

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