tributylphosphine; water in N,N-dimethyl-formamide 5 h;

1: 1) PCl5 / 1) 80 deg C, 30 min, 2) 30 min 2: NBS, dibenzoyl peroxide / CCl4 / 7 h / Heating 3: NaN3 / ethanol / 40 h / Ambient temperature 4: 57 percent / methanol / 6 h / Ambient temperature 5: 71 percent / K2CO3 / acetonitrile; H2O / 5 h / Ambient temperature 6: 65 percent / diisopropylcarbodiimide, 4-(N,N-dimethylamino)pyridine / dimethylformamide; CH2Cl2 / 17 h / Ambient temperature 7: n-Bu3P, H2O / dimethylformamide / 5 h View Scheme

1: NBS, dibenzoyl peroxide / CCl4 / 7 h / Heating 2: NaN3 / ethanol / 40 h / Ambient temperature 3: 57 percent / methanol / 6 h / Ambient temperature 4: 71 percent / K2CO3 / acetonitrile; H2O / 5 h / Ambient temperature 5: 65 percent / diisopropylcarbodiimide, 4-(N,N-dimethylamino)pyridine / dimethylformamide; CH2Cl2 / 17 h / Ambient temperature 6: n-Bu3P, H2O / dimethylformamide / 5 h View Scheme

1: 71 percent / K2CO3 / acetonitrile; H2O / 5 h / Ambient temperature 2: 65 percent / diisopropylcarbodiimide, 4-(N,N-dimethylamino)pyridine / dimethylformamide; CH2Cl2 / 17 h / Ambient temperature 3: n-Bu3P, H2O / dimethylformamide / 5 h View Scheme

1: 65 percent / diisopropylcarbodiimide, 4-(N,N-dimethylamino)pyridine / dimethylformamide; CH2Cl2 / 17 h / Ambient temperature 2: n-Bu3P, H2O / dimethylformamide / 5 h View Scheme

1: NaN3 / ethanol / 40 h / Ambient temperature 2: 57 percent / methanol / 6 h / Ambient temperature 3: 71 percent / K2CO3 / acetonitrile; H2O / 5 h / Ambient temperature 4: 65 percent / diisopropylcarbodiimide, 4-(N,N-dimethylamino)pyridine / dimethylformamide; CH2Cl2 / 17 h / Ambient temperature 5: n-Bu3P, H2O / dimethylformamide / 5 h View Scheme

1: 57 percent / methanol / 6 h / Ambient temperature 2: 71 percent / K2CO3 / acetonitrile; H2O / 5 h / Ambient temperature 3: 65 percent / diisopropylcarbodiimide, 4-(N,N-dimethylamino)pyridine / dimethylformamide; CH2Cl2 / 17 h / Ambient temperature 4: n-Bu3P, H2O / dimethylformamide / 5 h View Scheme

1: 98 percent / H2SO4 / toluene / 4 h / Heating 2: 99 percent / Na2CO3, H2O / 4 h / Heating 3: 12 percent / sodium persulfate, sodium acetate, copper(II) acetate monohydrate, CH3COOH / 8 h / Heating View Scheme

sodium peroxodisulphate; copper diacetate; sodium acetate; acetic acid 8 h; Heating;

sodium peroxodisulphate; copper diacetate; sodium acetate; acetic acid 8 h; Heating;