Chloroform → HCID 17989336, compound

HRID 1353079Notes

Reaction equation

HRID 1353079 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.CC(C)([O-])C.[K+].[CH:23](Cl)([Cl:25])[Cl:24]>CN(C=O)C.C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[C:10]([CH:23]([Cl:25])[Cl:24])[CH:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6212ChloroformHCID 22613Biphenyl, 4-chloro-4'-nitro-HCID 23665647Potassium tert-butoxide

Product 1

HCID 17989336HCID 17989336, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-73 °C

Procedure

4′-Chloro-4-nitro-biphenyl [J. Amer. Chem. Soc; 68; 1946; 404] (2.74 g, 11.7 mmol) was dissolved in DMF (20 ml) and THF (6 ml), then potassium t-butoxide 5.26 g (47 mmol) was added. The stirred mixture was cooled to −73° C. then a solution of chloroform in THF (6 ml) was slowly introduced, maintaining this temperature. After a further 1 minute, the reaction was quenched with acetic acid (5 ml). The mixture was poured into water (200 ml) and extracted with dichloromethane. The crude product was purified by flash chromatography on silica (using dichloromethane-hexane as eluents) to give 4′-chloro-3-(1,1-dichloro-methyl)-4-nitro-biphenyl in 63% yield;

Workup

  1. temperaturemaintaining this temperature
  2. customthe reaction was quenched with acetic acid (5 ml)
  3. additionThe mixture was poured into water (200 ml)
  4. extractionextracted with dichloromethane
  5. customThe crude product was purified by flash chromatography on silica (using dichloromethane-hexane as eluents)

Sources & evidence

ORD record
ord-223d4ec77faf41e2a34b76527d7f8d80
Source dataset
uspto-grants-2007_05
Patent number
US07220777B2

Reaction notes

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