1: (i) HNO2, (ii) CrO3 2: HCl / dioxane View Scheme

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '3587193', constants.ctx, '0')">bromine</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '3592982', constants.ctx, '0')">sodium methylate</a> <br /> <br /> &nbsp;

<b>Multi-step reaction with 2 steps<br /> </b>2: NaOMe, Br₂ <br /> <br /> &nbsp;

<b>Multi-step reaction with 3 steps<br /> </b>1: thionyl chloride / 4 h / 80 &deg;C<br />2: [{1,2-(tBu₂PCH₂)₂C₆H₄}Pd(OTf)](OTf); pyridine / 90 h / 90 &deg;C / 15001.5 Torr / |Schlenk technique; |Autoclave<br />3: hydrogen; potassium hydroxide; Grubb's 2nd generation catalyst / toluene / 40 h / 80 &deg;C / |Autoclave; |Schlenk technique<br /> <br /> &nbsp;