Ethyl Acetate → 1211594-32-9

HRID 1481362Notes

Reaction equation

HRID 1481362 reaction equation
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:5]=1Br.[C:13]([Cu])#[N:14].CCOC(C)=O.[OH-].[Na+]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl:10])[C:5]=1[C:13]#[N:14]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 53751442methyl 2-bromo-3-chlorobenzoateHCID 178418546HCID 178418546, compound

Product 1

HCID 552646011211594-32-9

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2-bromo-3-chlorobenzoic acid methyl ester (3.86 mmol) in 4 mL DMF was added CuCN (4.24 mmol) and the reaction mixture was heated to 90° C. overnight. After cooling to 10° C., 10 mL EtOAc and 3 mL 1M NaOH solution were added and stirring was continued at RT for 30 min. The aq. phase was separated and extracted twice with EtOAc. The combined organic layers were washed with brine, dried over MgSO4 and concentrated in vacuo. Purification by preparative LC-MS (method L) gives the desired product as white solid.

Workup

  1. temperatureAfter cooling to 10° C.
  2. customThe aq. phase was separated
  3. extractionextracted twice with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customPurification by preparative LC-MS (method L)

Sources & evidence

ORD record
ord-4d376949e42445cea456a98e96537fdd
Source dataset
uspto-grants-2016_08
Patent number
US09409917B2

Reaction notes

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