Diiodomethane → HCID 57779798, compound

HRID 1364203Notes

Reaction equation

HRID 1364203 reaction equation
[CH2:1]([Zn]CC)C.FC(F)(F)C(O)=O.ICI.[F:16][C:17]1[C:27]2[CH2:26][CH2:25][CH2:24][C:23](=[O:28])[N:22]([CH:29]=[CH2:30])[C:21]=2[C:20]([F:31])=[CH:19][C:18]=1[F:32].[NH4+].[Cl-]>C(Cl)Cl>[CH:29]1([N:22]2[C:23](=[O:28])[CH2:24][CH2:25][CH2:26][C:27]3[C:17]([F:16])=[C:18]([F:32])[CH:19]=[C:20]([F:31])[C:21]2=3)[CH2:1][CH2:30]1

Participants

7

Reactant 5

HCID 6346DiiodomethaneHCID 6422Trifluoroacetic acidHCID 25517Ammonium ChlorideHCID 57779774HCID 57779774, compoundHCID 178418750HCID 178418750, compound

Product 1

HCID 57779798HCID 57779798, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

An oven-dried 250 mL round-bottom flask was fitted with a stirbar and septa and flushed with nitrogen. Diethyl zinc (12.0 mL, 1.0 M/hexanes, 12.0 mmol) was added and cooled to 0° C. Trifluoroacetic acid (0.90 mL, 11.7 mmol) was added in a careful, dropwise manner over 5 minutes, and the reaction was then stirred for 15 minutes. Methylene chloride (10 mL) and diiodomethane (1.20 mL, 14.9 mmol) were then added, and the reaction was stirred for an additional 20 minutes. A solution of the product of Step 1 (1.01 g, 4.19 mmol) in methylene chloride (20 mL) was then added, and the reaction was stirred overnight with gradual warming to room temperature. After 25 hours, the reaction was poured into saturated aqueous NH4Cl solution (50 mL) and extracted with methylene chloride (3×50 mL). The organic extracts were combined, dried over MgSO4, filtered and concentrated in vacuo to give an oil that was purified via flash chromatography on silica gel (0% to 20% ethyl acetate/hexanes linear gradient) to give the desired product.

Workup

  1. customAn oven-dried 250 mL round-bottom flask was fitted with a stirbar and septa
  2. customflushed with nitrogen
  3. stirringthe reaction was stirred for an additional 20 minutes
  4. stirringthe reaction was stirred overnight
  5. temperaturewith gradual warming to room temperature
  6. waitAfter 25 hours
  7. extractionextracted with methylene chloride (3×50 mL)
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customto give an oil that
  12. customwas purified via flash chromatography on silica gel (0% to 20% ethyl acetate/hexanes linear gradient)

Sources & evidence

ORD record
ord-aec2f4345e7a4ef6be7aff64b7a8ebfb
Source dataset
uspto-grants-2011_02
Patent number
US07888345B2

Reaction notes

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