Dimethylformamide → t-Butyl 3-bromo-5-cyanobenzoate

HRID 269557Notes

Reaction equation

HRID 269557 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:12]=[C:13](I)[CH:14]=1)[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6].[CH3:16][N:17](C)C=O>[C-]#N.[Zn+2].[C-]#N.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH:12]=[C:13]([C:16]#[N:17])[CH:14]=1)[C:5]([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:6]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 574859731,1-Dimethylethyl 3-bromo-5-iodobenzoate

Product 1

HCID 69312160t-Butyl 3-bromo-5-cyanobenzoateYield 73%

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
80 °C

Procedure

A mixture of t-butyl 3-bromo-5-iodobenzoate (1.91 g, 5 mmol), zinc cyanide (585 mg, 5 mmol), and tetrakis(triphenylphosphine)palladium(0) (300 mg, 5 mol %) in dimethylformamide (20 ml) was heated at 80° C. for 2 hours. The solvent was evaporated. The residue was dissolved in ethyl acetate (20 ml) and washed with water and brine. The organic phase was dried and evaporated. Chromatography with ethyl acetate/hexane (1:4) gave the title compound as a colourless oil (1.02 g, 73%).

Workup

  1. customThe solvent was evaporated
  2. dissolutionThe residue was dissolved in ethyl acetate (20 ml)
  3. washwashed with water and brine
  4. customThe organic phase was dried
  5. customevaporated

Sources & evidence

ORD record
ord-960a87ef155a4261a08c9961438ceb7a
Source dataset
uspto-grants-2008_11
Patent number
US07446222B2

Reaction notes

Loading…