N-bromobutanimide → HCID 69517495, compound

HRID 855112Notes

Reaction equation

HRID 855112 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH3:14])[C:11]=1[O:12][CH3:13])[O:8][CH:7]([C:15]([F:18])([F:17])[F:16])[C:6]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:5]2.C1C(=O)N([Br:31])C(=O)C1>C(Cl)(Cl)(Cl)Cl>[Br:31][CH2:14][C:10]1[C:11]([O:12][CH3:13])=[C:2]([Cl:1])[CH:3]=[C:4]2[C:9]=1[O:8][CH:7]([C:15]([F:18])([F:16])[F:17])[C:6]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:5]2

Participants

4

Reactant 2

HCID 67184N-bromobutanimide2×HCID 69517852HCID 69517852, compound

Product 1

HCID 69517495HCID 69517495, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
60 °C

Procedure

The ethyl 6-chloro-7-methoxy-8-methyl-2-(trifluoromethyl)-2H-chromene-3-carboxylate from Example 3a, Step 3 (3.3 g, 9.4 mmole) was dissolved in CCl4 (30 mL) and the solution was heated to 60° C. NBS (1.84 g, 10.3 mmole) and Bzo2O (100 mg) were added to the above warm solution and the reaction was heated to reflux overnight. Additional NBS (1.84 g, 10.3 mmole) and Bzo2O (100 mg) were added to the above warm solution and the reaction was heated for 2 hrs. LCMS indicated that >95% product was formed. The reaction was cooled down and solid was filtered off. The filtrate was washed with NaHCO3 and brine. The organic layer was dried over anhydrous MgSO4 and evaporated to dry. The crude compound was used as crude (1H NMR indicated that the ratio of starting material/product is 40/60).

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux overnight
  3. temperaturethe reaction was heated for 2 hrs
  4. customwas formed
  5. temperatureThe reaction was cooled down
  6. filtrationsolid was filtered off
  7. washThe filtrate was washed with NaHCO3 and brine
  8. dry with materialThe organic layer was dried over anhydrous MgSO4
  9. customevaporated
  10. customto dry

Sources & evidence

ORD record
ord-da7a5b6d29674dfba84446e19e3bfb30
Source dataset
uspto-grants-2007_08
Patent number
US07259266B2

Reaction notes

Loading…