Iodoform → 1-Oxo-1-(4-chlorophenyl)-3-iodo-2-propene

HRID 54254

Reaction equation

HRID 54254 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH:10]=O)=[O:9])=[CH:4][CH:3]=1.[CH:12](I)(I)[I:13]>O1CCCC1.[Cl-].[Cl-].[Cr+2]>[O:9]=[C:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[CH:10]=[CH:12][I:13]

Participants

5

Reactant 2

HCID 6374IodoformHCID 269588(4-Chlorophenyl)(oxo)acetaldehyde

Product 1

HCID 543730961-Oxo-1-(4-chlorophenyl)-3-iodo-2-propene

Reagents, catalysts & solvents 2

HCID 10197677chromium(II) dichlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

This compound is prepared in a manner analogous to that of Step C of Example 4, using 6.7 grams (0.04 mole) of 4-chlorophenylglyoxal (prepared by the method of Kornblum et al., JACS, (1957), 79, 6562), 29.5 grams (0.24 mole) of anhydrous chromium(II) dichloride, and 31.5 grams (0.08 mole) of iodoform in 600 mL of tetrahydrofuran, yielding 1-oxo-1-(4-chlorophenyl)-3-iodo-2-propene.

Workup

  1. customThis compound is prepared in a manner analogous to that of Step C of Example 4

Sources & evidence

ORD record
ord-96efb8b9fa07495b9c0fddd1bf2d549f
Source dataset
uspto-grants-1997_04
Patent number
US05622954

Linked notes

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