Water → 1,1-Difluoro-1-(4-chlorophenyl)-3-iodo-2-propene

HRID 54252

Reaction equation

HRID 54252 reaction equation
[F:1][C:2]([F:12])([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1)[CH:3]=O.[CH:13](I)(I)[I:14].O>O1CCCC1.[Cl-].[Cl-].[Cr+2]>[F:1][C:2]([F:12])([C:5]1[CH:10]=[CH:9][C:8]([Cl:11])=[CH:7][CH:6]=1)[CH:3]=[CH:13][I:14]

Participants

6

Reactant 3

HCID 962WaterHCID 6374IodoformHCID 23237846Difluoro-4-chlorophenylacetaldehyde

Product 1

HCID 544227251,1-Difluoro-1-(4-chlorophenyl)-3-iodo-2-propene

Reagents, catalysts & solvents 2

HCID 10197677chromium(II) dichlorideCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Under a nitrogen atmosphere, a stirred suspension of 29.5 grams (0.24 mole) of anhydrous chromium(II) dichloride in 400 mL of tetrahydrofuran is cooled to 0° C., and a solution of 7.6 grams (0.04 mole) of difluoro-4-chlorophenylacetaldehyde and 31.5 grams (0.08 mole) of iodoform in 200 mL of tetrahydrofuran is added dropwise. Upon completion of addition, the reaction mixture is stirred at 0° C. for three hours. After this time the reaction mixture is poured into about 1200 mL of water, and the mixture is extracted with three 150 mL portions of diethyl ether. The combined extracts are dried with sodium sulfate and filtered. The filtrate is concentrated under reduced pressure, yielding 1,1-difluoro-1-(4-chlorophenyl)-3-iodo-2-propene.

Workup

  1. additionUpon completion of addition
  2. extractionthe mixture is extracted with three 150 mL portions of diethyl ether
  3. dry with materialThe combined extracts are dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-f7b1f32886c146759c5c2f973d915276
Source dataset
uspto-grants-1997_04
Patent number
US05622954

Linked notes

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