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Dimethylformamide → Methyl 5-cyano-3-methyl-1-benzofuran-2-carboxylate

HRID 2091152
Notes
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Reaction equation

HRID 2091152 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]([O:12][CH3:13])=[O:11])=[C:7]([CH3:14])[C:6]=2[CH:15]=1.[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.O>[C:16]([C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]([O:12][CH3:13])=[O:11])=[C:7]([CH3:14])[C:6]=2[CH:15]=1)#[N:17]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 6228DimethylformamideHCID 42967109Methyl 5-bromo-3-methylbenzofuran-2-carboxylate

Product 1

HCID 66778156Methyl 5-cyano-3-methyl-1-benzofuran-2-carboxylateYield 87%

Reagents, catalysts & solvents 3

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397
HCID 178418397, compound
Catalyst
HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of methyl 5-bromo-3-methyl-1-benzofuran-2-carboxylate (6.06 g) synthesized above, zinc cyanide (2.64 g) and N,N-dimethylformamide (60 mL) was added tetrakis(triphenylphosphine)palladium (0) (1.31 g), and the mixture was deaerated and stirred under argon atmosphere at 80° C. overnight. Water was added to quench the reaction, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was washed with diisopropyl ether to give the title object compound (4.20 g, 87%) as a pale-brown solid.

Workup

  1. customto quench
  2. customthe reaction
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. washThe residue was washed with diisopropyl ether

Sources & evidence

ORD record
ord-61b35804d6d44ce283aba98cde040213
Source dataset
uspto-grants-2013_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08436043B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes