Dimethylformamide → HCID 18797740, compound

HRID 463511Notes

Reaction equation

HRID 463511 reaction equation
P(Cl)(Cl)(Cl)=O.CN(C)[CH:8]=[O:9].[Br:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[O:19][CH:20]=[CH:21][CH:22]=2)=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Na+].[Na+]>ClC1C=CC=CC=1>[Br:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]2([O:19][CH:20]=[CH:21][CH2:22]2)[CH:8]=[O:9])=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 6228Dimethylformamide2×HCID 10340Sodium CarbonateHCID 24813Phosphorus oxychloride2×HCID 112761142-(4-bromophenyl)furan

Product 1

HCID 18797740HCID 18797740, compound

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

(Vilsmeir procedure) Phosphorous oxychloride POCL3 (12.5 g) and Dimethyl formamide (7 ml) were added to a mixture of 2(4-bromophenyl)furan (20.4 g) in chlorobenzene (100 ml). The mixture was stirred at 10° for one hour. A further addition of POCl3 (1.5 g) and DMF (0.7 g) was then made and the reaction stirred for a further one hour at RT. The mixture was poured onto ice, neutralised with sodium carbonate and the precipitated solid crystalised from chloroform (119). This solid was chromatographed on silica gel in chloroform to give 2(4-bromophenyl)furfural (11 g) m.p. 153.5°.

Workup

  1. stirringthe reaction stirred for a further one hour at RT
  2. additionThe mixture was poured onto ice
  3. customthe precipitated solid crystalised from chloroform (119)
  4. customThis solid was chromatographed on silica gel in chloroform

Sources & evidence

ORD record
ord-57afefb2373240c49e168becf37f880a
Source dataset
uspto-grants-1985_05
Patent number
US04520007

Reaction notes

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