Reaktion #45447

Reaktionsgleichung

4-bromo-2-iodo-phenylamine

thiacetamide

→

desired product

Ausbeute 48.2%

6-bromo-2-methyl-1,3-benzothiazole

Ausbeute 48.2%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigepartitioned between water and ethyl acetate
2. 2
   TrocknenThe organic phase was dried (Na2SO4)
3. 3
   Einengenconcentrated
4. 4
   SonstigeThe concentrate was purified by flash chromatography on silica gel using 20% hexanes/methylene chloride

Vorschrift

A solution of 4-bromo-2-iodo-phenylamine (1.5 g, 5.0 mmol), thiacetamide (381 mg, 5.0), cupric oxide (280 mg, 3.5 mmol), dppf (56 mg, 0.10 mmol), Pd2(dba)3 (48 mg, 0.052 mmol) in DMF was heated at 60° C. for 1 hour, cooled to room temperature, partitioned between water and ethyl acetate. The organic phase was dried (Na2SO4) and concentrated. The concentrate was purified by flash chromatography on silica gel using 20% hexanes/methylene chloride to give 550 mg (40% yield) of the desired product. MS (ESI(+)) m/e 227.8, 229.8 (M+H)+.

Quelle