Sodium Hydroxide → 3-Iodo-5-(trifluoromethyl)benzaldehyde

HRID 17058

Reaktionsgleichung

Reaktionsgleichung von HRID 17058
[I:1][C:2]1[CH:3]=[C:4]([CH2:12][OH:13])[CH:5]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:7]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH-].[Na+]>C(Cl)Cl>[I:1][C:2]1[CH:3]=[C:4]([CH:5]=[C:6]([C:8]([F:9])([F:10])[F:11])[CH:7]=1)[CH:12]=[O:13]

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 159087TriacetoxyperiodinaneHCID 192615723-Iodo-5-(trifluoromethyl)benzyl alcohol

Produkt 1

HCID 534147093-Iodo-5-(trifluoromethyl)benzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of [3-iodo-5-(trifluoromethyl)phenyl]methanol (287 mg, 0.95 mmol) in CH2Cl2 (10 mL) was cooled to 0° C. and then Dess-Martin periodinane (604 mg, 1.42 mmol) was added. The reaction was slowly warmed to room temperature. After stirring at room temperature for twenty minutes, the reaction was poured into 1N NaOH (25 mL). The mixture was extracted with EtOAc (50 mL) and the organic extracts were washed with brine (25 mL), dried over Na2SO4, filtered, and concentrated. Purification by flash chromatography with 0% to 10% EtOAc/hexanes afforded 3-iodo-5-(trifluoromethyl)benzaldehyde. Rf=0.54 (15% EtOAc/hexanes). 1H NMR (CDCl3, 600 MHz) δ 9.98 (s, 1H), 8.39 (s, 1H), 8.19 (s, 1H), 8.09 (s, 1H).

Aufarbeitung

  1. extractionThe mixture was extracted with EtOAc (50 mL)
  2. washthe organic extracts were washed with brine (25 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by flash chromatography with 0% to 10% EtOAc/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-9f39a994e7bf410e842925d20b4b4a44
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737295B2

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