Tin tetrachloride → HCID 57814503, compound

HRID 1715194Notes

Reaction equation

HRID 1715194 reaction equation
[Br:1][C:2]1[C:7]([Br:8])=[C:6]([N+:9]([O-])=O)[CH:5]=[C:4]([F:12])[C:3]=1[CH2:13][C:14]#[N:15].O.O.[Sn](Cl)Cl.[Sn](Cl)(Cl)(Cl)Cl.CCCCCC.C(OCC)(=O)C>C(O)C>[NH2:9][C:6]1[CH:5]=[C:4]([F:12])[C:3]([CH2:13][C:14]#[N:15])=[C:2]([Br:1])[C:7]=1[Br:8]

Participants

6

Reactant 4

HCID 24287Tin tetrachlorideHCID 61436Stannous chloride dihydrateHCID 21226206Ethyl acetate hexaneHCID 57814500HCID 57814500, compound

Product 1

HCID 57814503HCID 57814503, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
75 °C

Procedure

Twenty-four grams of a mixture containing (2,3-dibromo-6-fluoro-4-nitro-phenyl)-acetonitrile was dissolved in ethanol (500 mL) and tin (II) chloride dihydrate (85 g) was added. The mixture was stirred and heated at 75° C. for 5 h. 10 g more tin chloride was added and the mixture was heated at reflux for 30 additional minutes. The solution was cooled and most of the ethanol was removed in vacuo. The reaction mixture was diluted to a volume of 600 mL with ethyl acetate and 100 mL water was added. With stirring, sodium bicarbonate (75 g) was slowly added. The ethyl acetate layer was separated and the aqueous layer extracted a second time with ethyl acetate. The combined organic extracts were dried and the solvent removed in vacuo to afford 22.8 g of crude product. The title compound (3.8 g) was obtained from the crude mixture by column chromatography (hexane-ethyl acetate; then hexane-methylene chloride mixtures).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 30 additional minutes
  3. customwas removed in vacuo
  4. additionThe reaction mixture was diluted to a volume of 600 mL with ethyl acetate and 100 mL water
  5. additionwas added
  6. stirringWith stirring
  7. additionsodium bicarbonate (75 g) was slowly added
  8. customThe ethyl acetate layer was separated
  9. extractionthe aqueous layer extracted a second time with ethyl acetate
  10. customThe combined organic extracts were dried
  11. customthe solvent removed in vacuo
  12. customto afford 22.8 g of crude product

Sources & evidence

ORD record
ord-9698e5b19cf64ef4953c7e740ef391b9
Source dataset
uspto-grants-2010_09
Patent number
US07799816B2

Reaction notes

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