N-bromobutanimide → HCID 86674203, compound

HRID 241452Notes

Reaction equation

HRID 241452 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[C:12](=[O:15])[CH2:13][CH3:14].[Br:16]N1C(=O)CCC1=O>CCOCC>[Br:16][CH:13]([CH3:14])[C:12]([C:3]1[CH:4]=[CH:5][C:6]([C:8]([F:9])([F:10])[F:11])=[CH:7][C:2]=1[CH3:1])=[O:15]

Participants

4

Reactant 2

HCID 67184N-bromobutanimide3×HCID 71059804HCID 71059804, compound

Product 1

HCID 86674203HCID 86674203, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Add 1-[2-methyl-4-(trifluoromethyl)phenyl]propan-1-one (0.805 g, 3.723 mmol), N-bromosuccinimide (0.662 g, 3.723 mmol), SCX-2® (1 mmol/g; 0.298 g, 0.298 mmol), and Et2O (11 mL) to a screw cap vial equipped with a stir bar. Stir the reaction at room temperature for 2 hours. Add N-bromosuccinimide (0.663 g, 3.723 mmol) and continue stirring at room temperature for 2 hours. Add more N-bromosuccinimide (0.663 g, 3.723 mmol), and continue stirring at room temperature for an additional 2 hours. Filter the reaction, and wash the solids with ample Et2O. Collect the filtrate, and concentrate the filtrate under reduced pressure. Place the resulting mixture in a freezer overnight. Purify the resulting material by flash chromatography (120 RediSep® silica gel column) eluting with a gradient of 0-30% DCM/pentane to give the title compound as a colorless oil (0.820 g, 75% yield). 1H NMR (399.80 MHz, d6-DMSO) δ 7.95 (d, J=8.0 Hz, 1H), 7.69-7.65 (m, 2H), 5.64 (q, J=6.5 Hz, 1H), 2.39 (s, 3H), 1.74 (d, J=6.5 Hz, 3H).

Workup

  1. customcap vial
  2. customequipped with a stir bar
  3. customthe reaction at room temperature for 2 hours
  4. stirringcontinue stirring at room temperature for an additional 2 hours
  5. filtrationFilter
  6. customthe reaction
  7. washwash the solids with ample Et2O
  8. customCollect the filtrate
  9. concentrationconcentrate the filtrate under reduced pressure
  10. customin a freezer overnight
  11. customPurify the resulting material by flash chromatography (120 RediSep® silica gel column)
  12. washeluting with a gradient of 0-30% DCM/pentane

Sources & evidence

ORD record
ord-8bc42f124f1d473697b1f072ee8b0cd4
Source dataset
uspto-grants-2014_02
Patent number
US08648200B2

Reaction notes

Loading…