in ethylene glycol dimethyl ether; butan-1-ol 2 h; Yield given;

n-butyl chloride; lithium 1.) THF, sonication, 2.) THF, sonication, 6 h; Yield given. Multistep reaction;

1: 1.) butyl-lithium, di-isopropylamine / 1.) hexane, THF, -78 deg C --> room temp., 10 min; 2.) THF, -78 deg C; -20 deg C, 5 d 2: 58 percent / LiAlH4 / tetrahydrofuran / 2 h / 0 °C / 2.) room temp., overnight 3: pyridine / room temp., overnight 4: lithium bromide / tetrahydrofuran / room temp., overnight 5: 30 percent / tetrahydrofuran; liquid ammonia View Scheme

in acetonitrile 5 h; Heating;

1: 91 percent / acetonitrile / 5 h / Heating 2: 89 percent / acetonitrile / 15 h / Heating View Scheme

sodium iodide in acetone 12 h; Darkness;

in chloroform-d1 byproducts: I2; addn. of halogen to soln. of complex; amts. of products detected by (1)H-NMR;

in chloroform addn. of soln. of ICl in CHCl3 to soln. of Co-compd. in CHCl3 (darkness, room temp., N2 atmosphere, 45 min); concn., pouring into ether, filtration, washing (ether), chromy. (silica gel, CH2Cl2:MeOH:pyridine 90:9:1 vol/vol);

12 h; Ambient temperaturediff. solvents (ethyl acetate, benzene); Product distribution;