Water → HCID 10881471, Verbindung

HRID 1468482Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1468482
[I:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:11])([CH3:10])[CH3:9])=[CH:4][C:3]=1[OH:12].S(Cl)([Cl:16])(=O)=O.O>P(OC)(OC)(OC)=O>[Cl:16][C:6]1[C:5]([C:8]([CH3:9])([CH3:11])[CH3:10])=[CH:4][C:3]([OH:12])=[C:2]([I:1])[CH:7]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 24648Sulfuryl chlorideHCID 117478025-tert-Butyl-2-iodophenol

Produkt 1

HCID 10881471HCID 10881471, VerbindungAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 10541Trimethyl PhosphateLösungsmittel2×

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

To 35 mL of trimethyl phosphate (TMP) at 0° C. to 10° C. add 2-iodo-5-(1,1-dimethylethyl)phenol (6.61 g, 23.95 mmol, Preparation 42). To this solution add dropwise over the period of one minute sulfuryl chloride (2.0 mL, 24.67 mmol) in 35 mL of TMP, and then stir the resulting mixture for 30 minutes still at 0-10° C. To the reaction mixture add 130 mL of water, and then extract the resulting quenchate into CH2Cl2. Dry combined organic phases over anhydrous MgSO4, filter through silica gel, and concentrate filtrate. Purify residue by flash chromatography using 5% ethyl acetate in hexanes to give 3.79 g (51%) of 4-chloro-2-iodo-5-(1,1-dimethylethyl)phenol as a golden oil. 1H NMR (400 MHz, CDCl3) δ 7.58 (s, 1H), 7.05 (s, 1H), 5.21 (s, 1H), 1.43 (s, 9H). 13C NMR (101 MHz, CDCl3) δ 153.73, 149.02, 139.63, 125.69, 114.23, 81.61, 77.32, 76.68, 36.03, 29.29. MS m/e 310.

Aufarbeitung

  1. extractionextract the resulting quenchate into CH2Cl2
  2. customDry
  3. filtrationfilter through silica gel
  4. concentrationconcentrate filtrate

Quellen und Nachweise

ORD-Eintrag
ord-0559a113a5a643eda2b6ed6785629cce
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09000108B2

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