Dimethylformamide → HCID 10855492, compound

HRID 2226675Notes

Reaction equation

HRID 2226675 reaction equation
CN(C)[CH:3]=[O:4].[Mg].Br[C:8]1[CH:15]=[CH:14][CH:13]=[C:10]2[CH2:11][CH2:12][C:9]=12.[Cl-].[NH4+]>O1CCCC1>[CH:3]([C:8]1[CH:15]=[CH:14][CH:13]=[C:10]2[CH2:11][CH2:12][C:9]=12)=[O:4]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 117898682-Bromobicyclo[4.2.0]octa-1,3,5-triene

Product 1

HCID 10855492HCID 10855492, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The procedure is that of Evans, J. Chem. Soc. (1956), pages 4691-4693. Dimethylformamide (15 mL) is added dropwise to a stirred solution of Grignard reagent prepared from 4.8 g of magnesium and 18.3 g of 4-bromobenzocyclobutene in 40 mL of tetrahydrofuran at 0° C. under a nitrogen atmosphere. The resulting mixture is warmed slowly to room temperature and poured into 100 mL of saturated ammonium chloride solution. The mixture is extracted with ethyl acetate and the organic extract is washed with water and brine and then dried over anhydrous magnesium sulfate. After removing solvent, the product is distilled under reduced pressure to give 11.9 g (90%) of 4-formylbenzocyclobutene, b 90° C./3.5 mm.

Workup

  1. extractionThe mixture is extracted with ethyl acetate
  2. extractionthe organic extract
  3. washis washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customAfter removing solvent
  6. distillationthe product is distilled under reduced pressure

Sources & evidence

ORD record
ord-59bc18266ed64c2a8da39ae0a00f5ca5
Source dataset
uspto-grants-1994_09
Patent number
US05349095

Reaction notes

Loading…