phosphorus trichoride in dichloromethane T=20°C; 1.5 h; Inert atmosphereSchlenk technique;

2: methyl bromoacetate, MeONa / 72 h / Ambient temperature View Scheme

Yield given;

phosphorus pentachloride

[bis(acetoxy)iodo]benzene; sodium isopropanolate 1 h; Heating;

dihydrogen peroxide

iodosylbenzene 12 h; Heating;

1: 85 percent / CH2Cl2 / -85 to -80 deg C, 30 min, then 15-20 deg C, 5 h 2: 90 percent / triethylamine / CH2Cl2 / 0 - 5 deg C, 20 min, then 20 deg C, 4 h View Scheme

diisobutylaluminium hydride in tetrahydrofuran T=50°C; 4 h;

<b>With</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '3587154', constants.ctx, '0')">ammonia</a>;&nbsp;<a href="#" onclick="return RXDsubstances(event, this, '3647881', constants.ctx, '0')">sodium</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '102391', constants.ctx, '0')">tetrahydrofuran</a> <br />T=-78&deg;C;&nbsp;0.25&nbsp;h;&nbsp;<br /> &nbsp;