7-Bromo-2,3-dihydro-1-benzofuran-5-carbaldehyde → 5-Formyl-2,3-dihydro-1-benzofuran-7-carbonitrile

HRID 15362

Reaction equation

HRID 15362 reaction equation
Br[C:2]1[C:10]2[O:9][CH2:8][CH2:7][C:6]=2[CH:5]=[C:4]([CH:11]=[O:12])[CH:3]=1.[Cu][C:14]#[N:15]>CC(N(C)C)=O>[CH:11]([C:4]1[CH:3]=[C:2]([C:14]#[N:15])[C:10]2[O:9][CH2:8][CH2:7][C:6]=2[CH:5]=1)=[O:12]

Participants

4

Reactant 2

HCID 185261827-Bromo-2,3-dihydro-1-benzofuran-5-carbaldehydeHCID 178418546HCID 178418546, compound

Product 1

HCID 574869025-Formyl-2,3-dihydro-1-benzofuran-7-carbonitrileYield 61.4%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of 7-bromo-2,3-dihydro-1-benzofuran-5-carbaldehyde (1.3 g, 4.7 mmol) in dimethylacetamide (2 mL) was added copper(I) cyanide (0.41 g g, 4.7 mmol). The reaction was refluxed for 18 hours, and then concentrated under reduced pressure. The residue was washed well with warm ethyl acetate. The combined ethyl acetate layer were concentrated and dried. The crude product was purified by flash column chromatography (silica gel, 4:1 and 2:1 hexane:ethyl acetate gradient) to afford the desired product (0.5 g, 50%).

Workup

  1. temperatureThe reaction was refluxed for 18 hours
  2. concentrationconcentrated under reduced pressure
  3. washThe residue was washed well with warm ethyl acetate
  4. concentrationThe combined ethyl acetate layer were concentrated
  5. customdried
  6. customThe crude product was purified by flash column chromatography (silica gel, 4:1 and 2:1 hexane:ethyl acetate gradient)

Sources & evidence

ORD record
ord-e42717a54edc4e1c97f54229ecf0c95c
Source dataset
uspto-grants-2010_06
Patent number
US07732461B2

Linked notes

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