Methyl 2-(2-bromophenyl)acetate → Methyl(2-cyanophenyl)acetate

HRID 1612398Notes

Reaction equation

HRID 1612398 reaction equation
[Cu][C:2]#[N:3].[CH3:4][O:5][C:6](=[O:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1Br>CN(C)C=O.O.[Fe](Cl)(Cl)Cl>[CH3:4][O:5][C:6](=[O:15])[CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=1[C:2]#[N:3]

Participants

6

Reactant 2

HCID 8063364Methyl 2-(2-bromophenyl)acetateHCID 178418546HCID 178418546, compound

Product 1

HCID 1512623Methyl(2-cyanophenyl)acetate

Reagents, catalysts & solvents 3

HCID 24380Iron chloride (FeCl3)CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a stirring solution of copper (I) cyanide (1.2 eq) in dimethylformamide (2.1 M) at room temperature was added slowly a solution of 2a in dimethylformamide (8.7 M). The reaction was heated to reflux overnight then cooled to room temperature. A solution of iron (III) chloride (1.2 eq) in H2O (0.3 M) was added slowly to the vigorously stirred solution. The resulting solution was extracted with ethyl acetate (3×). The organic phases were combined then washed with brine (1×), dried over sodium sulfate, filtered, concentrated in vacuo and purified by flash chromatography (15% ethyl acetate/hexanes) to afford the product as a clear oil. (70%) 1H NMR (300 MHz, CDCl3) δ 6.09 (m, 1H), 5.98 (m, 1H), 5.79 (m, 2H), 2.29 (s, 2H), 2.11 (s, 3H).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux overnight
  3. extractionThe resulting solution was extracted with ethyl acetate (3×)
  4. washThe organic phases were combined then washed with brine (1×)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. custompurified by flash chromatography (15% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-5aa1c99be26a4bbd8d1b0b7de2924d43
Source dataset
uspto-grants-2006_01
Patent number
US06992193B2

Reaction notes

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