Bromine → 5-tert-Butyl-2-methyl-4-thiocyanato-phenol

HRID 356500Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 356500
[C:1]([C:5]1[CH:6]=[CH:7][C:8]([CH3:12])=[C:9]([OH:11])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[S:13](C#N)[C:14]#[N:15].[Na].[Br-].[Na+].BrBr>CO>[C:1]([C:5]1[C:6]([S:13][C:14]#[N:15])=[CH:7][C:8]([CH3:12])=[C:9]([OH:11])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

6

Edukt 4

HCID 24408BromineHCID 798455-tert-Butyl-o-cresolHCID 253881Sodium BromideHCID 86753328CID 86753328

Produkt 1

HCID 105609555-tert-Butyl-2-methyl-4-thiocyanato-phenol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

In a 5 L flask were placed 350 g (2.13 mol) of 5-tert-butyl-2-methyl-phenol, sodium thiocyanide (555 g, 6.85 mol) and MeOH (1400 mL), and the resulting mixture cooled to 7° C. A solution of sodium bromide (214 g, 2.08 mol), bromine (126 mL, 2.38 mol), and MeOH (1800 mL) was added slowly and the temperature raised to 40° C. over a period of 30 minutes. The precipitants were filtered and the filtrate concentrated by half. Saturated sodium carbonate (3.5 L) and H2O (4.5 L) were added. The mixture was extracted with EtOAc (3 L), and the organic layers were combined and concentrated. To this residue were added t-butylmethyl ether (500 mL) and hexanes (500 mL), and the mixture was allowed to stand for 17 hours at -5° C. The precipitants were filtered to give the title compound, m.p. 99°-102° C. 1H NMR (CDCl3) δ 1.46 (s, 9 H), 2.22 (s, 3 H), 5.01 (s, 1 H), 6.89 (s, 1 H), 7.49 (s, 1 H).

Aufarbeitung

  1. customIn a 5 L flask were placed
  2. filtrationThe precipitants were filtered
  3. concentrationthe filtrate concentrated by half
  4. additionSaturated sodium carbonate (3.5 L) and H2O (4.5 L) were added
  5. extractionThe mixture was extracted with EtOAc (3 L)
  6. concentrationconcentrated
  7. additionTo this residue were added t-butylmethyl ether (500 mL) and hexanes (500 mL)
  8. filtrationThe precipitants were filtered

Quellen und Nachweise

ORD-Eintrag
ord-aefea9b903b04ba99103150098733d61
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05834506

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