ethyl 4-(3-bromophenoxy)butanoate synthesis

Yield:157245-84-6 100%

Reaction Conditions:

with potassium carbonate in DMF (N,N-dimethyl-formamide) at 20 - 33; for 39 h;

Steps:

7.1

Potassium carbonate (319.0 g, 2.312 mol, 2 equiv) was added to a solution of 3-bromophenol (200 g, 1.156 mol, 1 equiv) and ethyl 4-bromobutryate (250 g, 1.282 mol, 1.11 equiv) in DMF (1.3 L). The reaction temperature increased from 28 to 33 C, then dropped back to room temperature. The suspension was stirred at room temperature for 39 h. The supernatant was decanted and the solids were slurried in HEPTANE/MTBE (tert-butyl methyl ether) (1.5 L, 2: 1 v/v) and filtered. The DMF solution was concentrated in vacuo to give an oil. The residual oil was partitioned between the heptane/MTBE washings and H20. The organic solution was washed sequentially with H2O (2 x 0.5 L), 1 N NAOH (2 x 1 L), H2O (4 x 0.5 L) and brine, then dried (NA2SO4), filtered and concentrated in vacuo. The resulting oil was placed under full vacuum for 1 h to give 336.7 g (102%) of ethyl 4- (3-BROMOPHENOXY) butyrate [BR-1182-1], which was used in the next step without further purification.

References:

WO2004/69245,2004,A1 Location in patent:Page/Page column 88-89