1-bromo-2-ethoxymethyl-4-hydroxymethylbenzene synthesis

Yield:-

Reaction Conditions:

Stage #1: ethyl 4-bromo-3-(ethoxymethyl)benzoatewith diisobutylaluminium hydride in toluene at -10; for 0.5 h;
Stage #2: with water;sodium hydroxide in toluene at 10;

Steps:

8

Example 8; l-Bromo-2-ethoxymethyl-4-hydroxymethylbenzene (Compound 17); [0063] To a solution of ethyl 4-bromo-3-ethoxymethylbenzoate (9.4 g, 33 mmol) in toluene (56 mL) at about -10 ⁰C was added 51 g of a 20% diisobutylaluminum hydride solution in toluene (ca. 70 mmol). The reaction was stirred at the same temperature for about 30 minutes until the reduction was completed, and then quenched with icy 5% NaOH solution to keep the temperature below about 10 °C. Organic phase of the resulting mixture was separated and the aqueous phase was extracted with toluene. The combined organic phase was concentrated in vacuo to a final volume of ~60 mL toluene solution of l-bromo-2-ethoxymethyl-4-hydroxymethylbenzene (Compound 17) that was used in next step without purification.

References:

WO2010/135350,2010,A2 Location in patent:Page/Page column 20-21