BrC1C=CC=C2C=1CC(=[O:11])C2.Br[C:13]1[CH:21]=[CH:20][CH:19]=[C:18]2[C:14]=1[CH2:15][C:16]([F:23])([F:22])[CH2:17]2.C(N(S(F)(F)F)CC)C.B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.C(OO)(=O)C>[Pd]>[F:22][C:16]1([F:23])[CH2:15][C:14]2[C:13]([OH:11])=[CH:21][CH:20]=[CH:19][C:18]=2[CH2:17]14-Bromo-1,3-dihydro-2H-inden-2-one was converted to 4-bromo-2,2-difluoroindane with (diethylamino)sulfur trifluoride. Palladium-catalyzed reaction with bis(pinacolato)diboron, followed by oxidation with peracetic acid, afforded 2,2-difluoroindan-4-ol.
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