N-bromobutanimide → HCID 14129197, compound

HRID 1504319Notes

Reaction equation

HRID 1504319 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 73%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a mixture of 2-fluoro-5-(trifluoromethoxy)aniline (2 g, 10 mmol) dissolved in DMF (4 mL) was slowly added a solution of N-bromosuccinimide (2.2 g, 12 mmol) dissolved in DMF (5 mL). The reaction mixture was stirred at RT for 1 h, concentrated and extracted with ethyl acetate/water. The organic layer was washed with brine, partitioned, dried over sodium sulfate, filtered, concentrated, and purified by silica chromatography (100% hexanes) to produce the title intermediate as a red oil (2 g, 70% yield). (m/z): [M+H]+ calcd for C7H4BrF4NO 273.94; 275.94. found 276.2.

Workup

  1. concentrationconcentrated
  2. extractionextracted with ethyl acetate/water
  3. washThe organic layer was washed with brine
  4. custompartitioned
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by silica chromatography (100% hexanes)

Sources & evidence

ORD record
ord-7c1ca5b0c37544888dac55de2b0ad400
Source dataset
uspto-grants-2015_12
Patent number
US09212168B2

Reaction notes

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