Methyl iodide → HCID 54010899, compound

HRID 2165217Notes

Reaction equation

HRID 2165217 reaction equation
[CH3:1]I.[Mg].C[C:5]1[C:12]([F:13])=[C:11]([F:14])[C:8]([CH:9]=[O:10])=[C:7]([F:15])[C:6]=1[F:16].[Cl-].[NH4+]>C(OCC)C>[CH3:1][CH:9]([OH:10])[C:8]1[C:7]([F:15])=[C:6]([F:16])[CH:5]=[C:12]([F:13])[C:11]=1[F:14]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 1326801291162-06-0

Product 1

HCID 54010899HCID 54010899, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

3 2 ml of methyl iodide were introduced over the course of 30 minutes into a suspension of 1 g of magnesium and 30 ml of ethyl ether and the mixture was stirred for 30 minutes. The mixture was cooled to 0° C. and 4 g of 4-methyl-2,3,5,6-tetra fluorobenzaldehyde and 100 ml of ethyl ether were introduced over the course of 30 minutes. The reaction mixture was stirred for 1 hour at 0° C. and was poured into 150 ml of a saturated aqueous ammonium chloride solution. Extraction was carried out with ether and the ethereal phases were dried and evaporated to dryness under reduced pressure. The crude product was chromatographed on silica and eluted with a hexane:isopropyl ether (8:2) mixture to obtain 3.85 g of the product with a Rf=0.10.

Workup

  1. stirringThe reaction mixture was stirred for 1 hour at 0° C.
  2. extractionExtraction
  3. customthe ethereal phases were dried
  4. customevaporated to dryness under reduced pressure
  5. customThe crude product was chromatographed on silica
  6. washeluted with a hexane:isopropyl ether (8:2) mixture

Sources & evidence

ORD record
ord-4b24874aac494aa9a688b1d0ad96eb3c
Source dataset
uspto-grants-1990_07
Patent number
US04939172

Reaction notes

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