in hexane; toluene 1) 0 deg C, 1 h, 2) RT, 18 h;

1: oxalyl chloride / CH2Cl2 / 24 h / Ambient temperature 2: 99 percent / toluene; hexane / 1) 0 deg C, 1 h, 2) RT, 18 h View Scheme

1: 65 percent / CuBr, aq. HBr, NaNO2 / 1) 90 deg C, 1 h, 2) reflux, 0.5 h, 3) RT, 2 h 2: oxalyl chloride / CH2Cl2 / 24 h / Ambient temperature 3: 99 percent / toluene; hexane / 1) 0 deg C, 1 h, 2) RT, 18 h View Scheme