trimethylsilyl bromide in chloroform 50 deg C, 8 h; 20 deg C, 12 h;

1: 96 percent / Na2Cr2O7 / H2O / 6 h / 250 °C 2: 17 percent / NaBH4, 45percentBF3*Et2O / bis-(2-methoxy-ethyl) ether / 3 h / 50 °C 3: 88 percent / BrSi(CH3)3 / CHCl3 / 50 deg C, 8 h; 20 deg C, 12 h View Scheme

1: 17 percent / NaBH4, 45percentBF3*Et2O / bis-(2-methoxy-ethyl) ether / 3 h / 50 °C 2: 88 percent / BrSi(CH3)3 / CHCl3 / 50 deg C, 8 h; 20 deg C, 12 h View Scheme

1: 1) hydrochinone, 2) 5percent KOH / 1) C2H5OH, 6 h, 130 deg C, 2) C2H5OH, 8 h, 40-50 deg C; 12 h, RT 2: 96 percent / Na2Cr2O7 / H2O / 6 h / 250 °C 3: 17 percent / NaBH4, 45percentBF3*Et2O / bis-(2-methoxy-ethyl) ether / 3 h / 50 °C 4: 88 percent / BrSi(CH3)3 / CHCl3 / 50 deg C, 8 h; 20 deg C, 12 h View Scheme

1: 97 percent / LiAlH4 / tetrahydrofuran / 24 h 2: 88 percent / BrSi(CH3)3 / CHCl3 / 50 deg C, 8 h; 20 deg C, 12 h View Scheme

1: 91 percent / DDQ / benzene / 1 h / Heating 2: 97 percent / LiAlH4 / tetrahydrofuran / 24 h 3: 88 percent / BrSi(CH3)3 / CHCl3 / 50 deg C, 8 h; 20 deg C, 12 h View Scheme