Br[C:2]1[CH:7]=[C:6]([O:8][CH:9]([CH3:11])[CH3:10])[CH:5]=[C:4]([O:12][CH:13]([CH3:15])[CH3:14])[CH:3]=1.[Li]CCCC.[I:21]I>C1COCC1.CCOC(C)=O>[I:21][C:2]1[CH:7]=[C:6]([O:8][CH:9]([CH3:11])[CH3:10])[CH:5]=[C:4]([O:12][CH:13]([CH3:15])[CH3:14])[CH:3]=1To a solution of 1-bromo-3,5-bis(propan-2-yloxy)benzene (46) (2.0 g, 7.3 mmol) in THF (100 mL), cooled to −78° C., a 1.6 M n-BuLi solution in hexanes (9.16 mL, 14.7 mmol) was added dropwise. The temperature was maintained at −78° C. for 30 min, after which a solution of iodine (3.17 g, 29.3 mmol) in THF (15 mL) was added dropwise. The mixture was warmed to −35° C. and maintained at this temperature for 1.5 h. The reaction mixture was diluted with EtOAc (100 mL) and washed with water (2×50 mL) and brine (50 mL). The organic layer was separated, dried (Na2SO4) and concentrated. Purification by column chromatography on silica gel (Hexanes/EtOAc, 4:1) gave 1-iodo-3,5-bis(propan-2-yloxy)benzene (47) (1.85 g, 79%) as a viscous orange oil.
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