N-bromobutanimide → HCID 11392096, compound

HRID 1989821Notes

Reaction equation

HRID 1989821 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10]([CH3:14])([CH3:13])[C:11]#[N:12].[Br:15]N1C(=O)CCC1=O>C(O)(C(F)(F)F)=O>[Br:15][C:5]1[C:6]([O:8][CH3:9])=[CH:7][C:2]([Cl:1])=[C:3]([C:10]([CH3:14])([CH3:13])[C:11]#[N:12])[CH:4]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 11401556HCID 11401556, compound

Product 1

HCID 11392096HCID 11392096, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 2-(2-chloro-4-methoxy-phenyl)-2-methyl-propionitrile (17.5 g, 0.0835 mol) in TFA (100 mL) was cooled to 0° C. N-bromosuccinimide (14.9 g, 0.0835 mol) was added in small portions keeping the temperature below 5° C. The orange solution was stirred for 2 h/25° C. and evaporated to dryness. Water (200 mL) was added and the mixture was stirred vigorously for 1 h. The crude product was filtered off and recrystallized from boiling MeOH. The pure product was isolated as white needles. Yield: 13 g (54%). GCMS: >99%

Workup

  1. customthe temperature below 5° C
  2. customevaporated to dryness
  3. additionWater (200 mL) was added
  4. stirringthe mixture was stirred vigorously for 1 h
  5. filtrationThe crude product was filtered off
  6. customrecrystallized
  7. customThe pure product was isolated as white needles

Sources & evidence

ORD record
ord-3d621602a26746aca884dbd4299d5263
Source dataset
uspto-grants-2010_01
Patent number
US07642367B2

Reaction notes

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