N-bromobutanimide → HCID 66819934, compound

HRID 2173185Notes

Reaction equation

HRID 2173185 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 5-bromo-2-benzofuran-1(3H)-one (12.0 g, 56.3 mmol) and NBS (15 g, 84 mmol). Triflic acid (50 mL) was then added at 0° C. and the resulting mixture was allowed to warm to rt and stir for 2 days. TLC analysis of the reaction mixture showed complete reaction. The reaction mixture was poured into ice and the organic layer was separated, washed with brine, water, dried over Na2SO4, filtered, and concentrated to dryness. The residue was then absorbed into silica gel and subjected for purification over a silica MPLC column to give 4,5-dibromo-2-benzofuran-1(3H)-one. LC-MS (IE, m/z): 291 [M+1]+.

Workup

  1. additionTo a flask containing a stir bar
  2. customreaction
  3. additionThe reaction mixture was poured into ice
  4. customthe organic layer was separated
  5. washwashed with brine, water
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated to dryness
  9. customThe residue was then absorbed into silica gel
  10. customsubjected for purification over a silica MPLC column

Sources & evidence

ORD record
ord-19881afd43914db296315f427d2c83ff
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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