HCID 68869194, compound → HCID 68871558, compound

HRID 2105835Notes

Reaction equation

HRID 2105835 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[C:5]1[CH:10]=[C:9](Br)[C:8]([Cl:12])=[CH:7][C:6]=1[O:13][CH2:14][CH3:15])[CH3:2].[Cu][C:18]#[N:19]>CN(C)C=O.C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:16])[C:5]1[CH:10]=[C:9]([C:18]#[N:19])[C:8]([Cl:12])=[CH:7][C:6]=1[O:13][CH2:14][CH3:15])[CH3:2]

Participants

5

Reactant 2

HCID 68869194HCID 68869194, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 68871558HCID 68871558, compoundYield 47.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-bromo-4-chloro-2-ethoxy-benzoic acid ethyl ester (940 mg, 3.0 mmol) in 20 mL of dimethylformamide was added copper(I) cyanide (327 mg, 3.65 mmol). The reaction was stirred at reflux overnight. The reaction was diluted with methylene chloride. It was washed twice with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. Purification of the crude residue by flash column chromatography (silica gel, eluting with a gradient of ethyl acetate in hexanes) gave 4-chloro-5-cyano-2-ethoxy-benzoic acid ethyl ester (359 mg, 47%). LC-MS: 254.1 [(M+H)+].

Workup

  1. temperatureat reflux overnight
  2. washIt was washed twice with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customPurification of the crude residue by flash column chromatography (silica gel
  6. washeluting with a gradient of ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-d8b89554aeb1499d91c08ba4100a8c54
Source dataset
uspto-grants-2009_08
Patent number
US07579368B2

Reaction notes

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