Bromine → HCID 66955137, compound

HRID 1948536Notes

Reaction equation

HRID 1948536 reaction equation
[C:1]([C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][CH:7]=1)(=[O:5])[CH:2]([CH3:4])[CH3:3].[Br:14]Br>C(O)(=O)C>[Br:14][C:2]([CH3:4])([CH3:3])[C:1]([C:6]1[CH:7]=[CH:8][C:9]([C:10]#[N:11])=[CH:12][CH:13]=1)=[O:5]

Participants

4

Reactant 2

HCID 24408BromineHCID 13445263HCID 13445263, compound

Product 1

HCID 66955137HCID 66955137, compoundYield 71.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of 4-isobutyrylbenzonitrile (2.4 g, 13.86 mmol) in acetic acid (50 mL) was added bromine (0.8 mL, 15.53 mmol). The mixture was stirred for 3 days and then concentrated in vacuo. The reaction mixture was diluted with ethyl acetate and washed with sat NaHCO3. The organic layer was dried MgSO4, filtered, concentrated, and then purified on silica gel using an EtOAc/hexanes gradient to yield 2.5 g of 4-(2-bromo-2-methylpropanoyl)benzonitrile. 1H NMR (400 MHz, chloroform-d) δ ppm 8.00-8.07 (2H, m), 7.76-7.79 (2H, m), 1.24 (3H, s), 1.22 (3H, s).

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe reaction mixture was diluted with ethyl acetate
  3. washwashed
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified on silica gel using an EtOAc/hexanes gradient

Sources & evidence

ORD record
ord-3d0a29ee3f924060bf5e3b8271bd0b2e
Source dataset
uspto-grants-2013_03
Patent number
US08399451B2

Reaction notes

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