Hydrochloric Acid → HCID 68569266, compound

HRID 747603Notes

Reaction equation

HRID 747603 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[Zn]I.[N+:10]([C:13]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:14]=1[CH:15]=[O:16])([O-:12])=[O:11].C[Si](Cl)(C)C.Cl>C1COCC1.[Cl-].[Cl-].[Cl-].[Cr+3]>[N+:10]([C:13]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][C:14]=1[C:15]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1])=[O:16])([O-:12])=[O:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6397ChlorotrimethylsilaneHCID 5870905-Fluoro-2-nitrobenzaldehydeHCID 178478046HCID 178478046, compound

Product 1

HCID 68569266HCID 68569266, compound

Reagents, catalysts & solvents 2

HCID 6452300Chromium(3+) trichlorideCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
65 °C

Procedure

To 2.6 g of chromium trichloride suspended in 50 ml of THF are successively added 30 ml of a 0.5M solution in THF of 2-chlorophenyliodozinc, 2.54 g of 2-nitro-5-fluorobenzaldehyde and 5.7 ml of trimethylsilyl chloride. The mixture is heated at 65° C. for 1 hour and then left at room temperature for 18 hours. 1M hydrochloric acid solution is added to the reaction medium, the precipitate formed is filtered off and the filtrate is concentrated. The residue is taken up in ethyl acetate and washed with water. The organic phase is dried over anhydrous sodium sulfate and concentrated. The residue is chromatographed on a column of silica gel, eluting with cyclohexane, to give 1 g of the expected product.

Workup

  1. customthe precipitate formed
  2. filtrationis filtered off
  3. concentrationthe filtrate is concentrated
  4. washwashed with water
  5. dry with materialThe organic phase is dried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe residue is chromatographed on a column of silica gel
  8. washeluting with cyclohexane

Sources & evidence

ORD record
ord-3178c246512c4b7e9f269be7a57a4f2c
Source dataset
uspto-grants-2008_07
Patent number
US07396958B2

Reaction notes

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