C[O:2][C:3]([C:5]1[CH:6]=[C:7]([Br:14])[C:8]2[O:12][CH:11]=[CH:10][C:9]=2[CH:13]=1)=O.[H-].C([Al+]CC(C)C)C(C)C.[F-].[Na+].O>ClCCl>[OH:2][CH2:3][C:5]1[CH:6]=[C:7]([Br:14])[C:8]2[O:12][CH:11]=[CH:10][C:9]=2[CH:13]=1
A solution of 1.1 gm (4.31 mMol) 5-(methoxycarbonyl)-7-bromobenzofuran in 20 ml dichloromethane was cooled to −78° C. To this solution were then added 2.7 ml (15.1 mMol) diisobutylaluminum hydride. The reaction mixture was allowed to warm to room temperature and was then stirred for 10 minutes. To the reaction mixture were then added 2.5 gm sodium fluoride and 815 μL water. The resulting mixture was diluted with an additional 10 ml dichloromethane and was then stirred for about 1 hour. The suspension was filtered and the filtrate concentrated under reduced pressure to provide 0.50 gm (51%) of the desired compound. The recovered solid was partitioned between 200 ml ethyl acetate and 100 ml Rochelle's Salt solution for 2 hours. This mixture was filtered, the phases separated, and the organic phase concentrated under reduced pressure to provide an additional 0.30 gm (31%) of the desired compound.
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