N-bromobutanimide → HCID 66819934, compound

HRID 1501951Notes

Reaction equation

HRID 1501951 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[O:7][CH2:8][C:4]=2[CH:3]=1.C1C(=O)N([Br:19])C(=O)C1>OS(C(F)(F)F)(=O)=O>[Br:19][C:3]1[C:4]2[CH2:8][O:7][C:6](=[O:9])[C:5]=2[CH:10]=[CH:11][C:2]=1[Br:1]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 6031445-Bromophthalide

Product 1

HCID 66819934HCID 66819934, compound

Reagents, catalysts & solvents 1

HCID 62406Trifluoromethanesulfonic acidSolvent

Procedure

To a flask containing a stir bar was added commercially available 5-bromo-2-benzofuran-1(3H)-one (12.0 g, 56.3 mmol) and NBS (15 g, 84 mmol). Triflic acid (50 mL) was added at 0° C. and the resulting mixture was stirred for 2 days. TLC analysis of the reaction mixture showed a complete reaction; the reaction mixture was poured into an ice and the organic layer separated. The organic layer was washed with aq. NaCl, water, dried over Na2SO4, filtered and concentrated to dryness, it was then absorbed onto silica gel and subjected for purification over a silica column to give the title compound.

Workup

  1. additionTo a flask containing a stir bar
  2. customa complete reaction
  3. customthe organic layer separated
  4. washThe organic layer was washed with aq. NaCl, water
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness, it
  8. customwas then absorbed onto silica gel
  9. customsubjected for purification over a silica column

Sources & evidence

ORD record
ord-1b439fe8a87545649af5498d7e9fbd4a
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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