HCID 10801230, compound → HCID 67407512, compound

HRID 1913424Notes

Reaction equation

HRID 1913424 reaction equation
[CH3:1][O:2][C:3](=[O:14])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:6]=1Br.[Cu][C:16]#[N:17]>CN1CCCC1=O>[CH3:1][O:2][C:3](=[O:14])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:6]=1[C:16]#[N:17]

Participants

4

Reactant 2

HCID 10801230HCID 10801230, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 67407512HCID 67407512, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
170 °C

Procedure

To a microwave vial was added (2-bromo-4-methoxy-phenyl)-acetic acid methyl ester (200 mg, 0.77 mmol), copper (I) cyanide (138 mg, 1.54 mmol), a stir bar and 1 mL of N-methyl-pyrrolidinone. The vial was capped and heated at 170° C. for 15 minutes in a microwave reactor. The resulting dark solution was purified directly on an ISCO (Teledyne Isco Inc., Lincoln Nebr.) 12 g column using a 0-20% MeOH in dichloromethane gradient. The desired product eluted in 100% dichloromethane to give 120 mg (76%) of (2-cyano-4-methoxy-phenyl)-acetic acid methyl ester as an orange oil.

Workup

  1. customThe vial was capped
  2. customThe resulting dark solution was purified directly on an ISCO (Teledyne Isco Inc., Lincoln Nebr.) 12 g column
  3. washThe desired product eluted in 100% dichloromethane

Sources & evidence

ORD record
ord-48c4c1c832174ee7bedcab8e17945ee1
Source dataset
uspto-grants-2013_12
Patent number
US08609680B2

Reaction notes

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