Dimethylformamide → Dibenzofuran-3-carbaldehyde

HRID 1371844Notes

Reaction equation

HRID 1371844 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=3[O:7][C:6]=2[CH:14]=1.C([Li])(C)(C)C.CCCCCC.CN(C)[CH:28]=[O:29]>O1CCCC1>[CH:4]1[C:5]2[C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=3[O:7][C:6]=2[CH:14]=[C:2]([CH:28]=[O:29])[CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8058HexaneHCID 2968613-BromodibenzofuranHCID 178418306HCID 178418306, compound

Product 1

HCID 13474591Dibenzofuran-3-carbaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

Combine 3-bromodibenzofuran (0.5 g, 2.0 mmol) and tetrahydrofuran (30 ml). Cool to about −78° C. Add a solution of t-butyllithium, 1.6 M solution in hexane (2.2 ml, 3.0 mmol), then warm to about 0° C. for 10 min. Cool to about −78° C. and add dimethylformamide (0.5 ml, 5.9 mmol). Warm to room temperature, quench with water, and extract with dichloromethane. Combine the organic layers and wash sequentially with distilled water and brine and then dry (Na2SO4), filter, and concentrate to give a residue. Chromatograph the residue eluting with 8:2 hexane:EtOAc to give the title compound.

Workup

  1. temperaturewarm to about 0° C. for 10 min
  2. temperatureCool to about −78° C.
  3. temperatureWarm to room temperature
  4. customquench with water
  5. extractionextract with dichloromethane
  6. washwash sequentially with distilled water and brine
  7. dry with materialdry (Na2SO4)
  8. filtrationfilter
  9. concentrationconcentrate
  10. customto give a residue
  11. washChromatograph the residue eluting with 8:2 hexane

Sources & evidence

ORD record
ord-87710eb67c70482880d8f4e5b7546b4e
Source dataset
uspto-grants-2007_01
Patent number
US07157488B2

Reaction notes

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