Multi-step reaction with 11 steps
1: benzene / 2 h / 65 °C
2: 1.) aq. NaOH / 1.) EtOH, 30 min, 2.) ETOH, 1 h
3: 2.) 1,8-diazabicyclo<5.4.0>undec-7-ene, 3.) KOtBu
4: NaH / dimethylformamide / 2 h / Ambient temperature
5: aq. KOH / dimethylsulfoxide / 8 h / Heating
6: toluene / 1 h / Heating
7: benzene / 48 h / Ambient temperature
8: tetrahydrofuran / 1 h / 0 °C
9: aq. NH4OH / tetrahydrofuran / 1 h / Ambient temperature
10: BBr3 / CH2Cl2 / 1 h / 0 °C
11: K2CO3, KI / dimethylformamide / 5 h
With
potassium hydroxide; ammonium hydroxide; sodium hydroxide; potassium tert-butylate; boron tribromide; sodium hydride; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; potassium iodide;
In
tetrahydrofuran; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; benzene;
DOI:10.1021/jm960395q