Br[C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[CH:3]=1.CC1C=C(C=C(C)C=1CC1C=CC(OCOC)=C(CC2C=CC(F)=CC=2)C=1)C(OC)=O>[Pd].CO>[F:16][C:13]1[CH:12]=[CH:11][C:10]([CH2:9][C:4]2[CH:3]=[CH:2][CH:7]=[CH:6][C:5]=2[OH:8])=[CH:15][CH:14]=1A mixture of 4-bromo-2-(4-fluorobenzyl)phenol (compound 78, step a, 6.0 gm, 21.4 mmol), 1.2 g of palladium on activated carbon (10%) and 100 mL of methanol in a glass reaction vessel was shaken at 50 psi H2 over night, filtered and concentrated under reduced pressure. The resulting light orange oil was dissolved in 180 mL dichloromethane and washed 1× with NaHCO3 saturated solution. The organic was dried over Na2SO4, filtered and concentrated under reduced pressure to afford 2-(4-fluorobenzyl)phenol (4.52 gm, 100%): 1H NMR (200 MHz, DMSO-d6): δ 9.39 (s, 1H), 7.22 (m, 2H), 7.02 (m, 3H), 6.74 (m, 2H), 3.84 (s, 2H); TLC conditions: Uniplate silica gel, 250 microns; Mobile phase=methylene chloride-hexanes (1:1); Rf=0.32.
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