[C:1]([O:5][C:6]1[CH:7]=[C:8]([CH2:12][OH:13])[CH:9]=[CH:10][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[Br:14][CH2:15][CH2:16][CH2:17][CH2:18]Br>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.[OH-].[Na+].C1C=CC=CC=1>[Br:14][CH2:15][CH2:16][CH2:17][CH2:18][O:13][CH2:12][C:8]1[CH:9]=[CH:10][CH:11]=[C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])[CH:7]=1To a solution of (3-tert-butoxy-phenyl) methanol (4.02 g, 0.022 mol) and tetrabutylammonium hydrogen sulfate (0.379 g, 0.00115 mol) in 50% NaOH solution (6 mL) and benzene (15 mL) Was added 1,4-dibromobutane (7.99 mL, 0.067 mol) with vigorous stirring at ambient temperature. After stirring for 8 h, the mixture was partitioned between H2O and EtOAc. The organic layer was separated, washed with brine, dried (MgSO4), filtered, and concentrated to give the title compound after purification on an ISCO Combiflash eluting with 0-10% EtOAc/hexane.
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