4-(4-Bromophenyl)Thiomorpholine synthesis
- Product Name:4-(4-Bromophenyl)Thiomorpholine
- CAS Number:90254-20-9
- Molecular formula:C10H12BrNS
- Molecular Weight:258.18
Yield:90254-20-9 81%
Reaction Conditions:
with tris-(dibenzylideneacetone)dipalladium(0);potassium tert-butylate;2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl in toluene at 86;Inert atmosphere;
Steps:
A Step A: 4-(4-Bromophenyl)thiomorpholine
To the solution of thiomorpholine (7 g, 67.8 mmol) in toluene (170 mL) in a 500 mL round bottom flask under 2 were added 1 ,4-dibromobenzene (20.8 g, 88 mmol), Pd2(dba)3 (1.55 g, 1.7 mmol), BINAP (2.112 g, 3.39 mmol), and tert- uOK (16.3 g, 170 mmol). The reaction mixture was heated at 86 °C for 1.5-2 h. The reaction mixture was quenched with water (600 mL). The resulting mixture was extracted with EtOAc (3 x 600 mL). The combined organic fractions were washed with brine (600 mL), dried (MgS04), filtered, and solvent was removed under reduced pressure. The residue was purified by flash chromatography on ISCO silica gel column (Hexane/EtOAc (0-10%) giving 14.1 g (81% ) of the 4-(4-bromophenyl)thiomorpholine as light yellow solid.
References:
WO2015/51479,2015,A1 Location in patent:Page/Page column 54
55330-78-4
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