1: H2SO4, aq. HBr / 6 h / Heating 2: (i) NaOEt, EtOH, (ii) /BRN= 2425374/, (iii) KOH, (iv) (heating) 3: TsOH / CCl4 / Heating 4: (i) Mg, ether, BrCH2CH2Br, (ii) /BRN= 2462934/ 5: (i) TsOH, benzene, (ii) H2, Pt-C View Scheme

1: H2SO4, aq. HBr / 6 h / Heating 2: (i) NaOEt, EtOH, (ii) /BRN= 2425374/, (iii) KOH, (iv) (heating) 3: TsOH / CCl4 / Heating 4: (i) Mg, ether, BrCH2CH2Br, (ii) /BRN= 2462934/ 5: (i) TsOH, benzene, (ii) H2, Pt-C, cyclohexane View Scheme

1: H2SO4, aq. HBr / 6 h / Heating 2: (i) NaOEt, EtOH, (ii) /BRN= 2425374/, (iii) KOH, (iv) (heating) 3: TsOH / CCl4 / Heating 4: (i) Mg, ether, BrCH2CH2Br, (ii) /BRN= 2462934/ 5: (i) TsOH, benzene, (ii) H2, Pt-C View Scheme