1.1: 75 percent / Na2S2O4 / 2-methoxy-ethanol; H2O / 3 h / 110 °C 2.1: H2SO4 / H2O / 1 h / 80 °C 2.2: NaNO2 / H2O / 3 h / 20 °C 2.3: 82 percent / H3PO2 / H2O / 12 h / 20 °C View Scheme

1.1: SnCl2·2H2O / ethanol; tetrahydrofuran / 3 h / 20 °C 1.2: 1.5 h 2.1: hydrogenchloride / water / 0.33 h 2.2: 2 h / 0 - 5 °C 2.3: 0 - 20 °C 3.1: tert.-butyl lithium / pentane; tetrahydrofuran / 2 h / -80 - -76 °C 3.2: -80 °C 3.3: pH 1 View Scheme

sodium dithionite in 2-methoxy-ethanol; water T=110°C; 3 h;

1.1: SnCl2·2H2O / ethanol; tetrahydrofuran / 3 h / 20 °C 1.2: 1.5 h 2.1: hydrogenchloride / water / 0.33 h 2.2: 2 h / 0 - 5 °C 2.3: 0 - 20 °C 3.1: tert.-butyl lithium / pentane; tetrahydrofuran / 2 h / -80 - -76 °C 3.2: -80 °C 3.3: pH 1 4.1: thionyl chloride / toluene / 2 h / Reflux View Scheme

1.1: SnCl2·2H2O / ethanol; tetrahydrofuran / 3 h / 20 °C 1.2: 1.5 h 2.1: hydrogenchloride / water / 0.33 h 2.2: 2 h / 0 - 5 °C 2.3: 0 - 20 °C 3.1: tert.-butyl lithium / pentane; tetrahydrofuran / 2 h / -80 - -76 °C 3.2: -80 °C 3.3: pH 1 4.1: thionyl chloride / toluene / 2 h / Reflux 5.1: ammonia / toluene; tetrahydrofuran / 1 h 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, '4122945', constants.ctx, '0')">iron</a>&nbsp;<b>in</b>&nbsp; <a href="#" onclick="return RXDsubstances(event, this, '1731042', constants.ctx, '0')">chloroform</a> <br />T=50&deg;C;&nbsp;24&nbsp;h;&nbsp;<br /> &nbsp;