N-bromobutanimide → 2-(3-Bromo-4-methoxyphenyl)-2-methylpropionitrile

HRID 1989815Notes

Reaction equation

HRID 1989815 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([CH3:13])([CH3:12])[C:10]#[N:11])=[CH:5][CH:4]=1.[Br:14]N1C(=O)CCC1=O>C(O)(C(F)(F)F)=O>[Br:14][C:4]1[CH:5]=[C:6]([C:9]([CH3:13])([CH3:12])[C:10]#[N:11])[CH:7]=[CH:8][C:3]=1[O:2][CH3:1]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 2191662-(4-Methoxyphenyl)-2-methylpropanenitrile

Product 1

HCID 113688102-(3-Bromo-4-methoxyphenyl)-2-methylpropionitrile

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 2-(4-methoxy-phenyl)-2-methyl-propionitrile (17.5 g, 0.10 mol) in TFA (80 mL) was cooled to 0° C. N-bromosuccinimide (17.8 g, 0.10 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: 19.3 g (76%). 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-c9ede26dd7b74975a1adf6732b5b16f1
Source dataset
uspto-grants-2010_01
Patent number
US07642367B2

Reaction notes

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