[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[C:10]([OH:15])=[CH:11][CH:12]=[CH:13][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].C(Br)C=C.[CH2:26]([O:29]CC=C)[CH:27]=[CH2:28].C(C1C=CC=C(C2C(F)=CC=CC=2F)C=1O)C=C.ClC1C=C(C=CC=1)C(OO)=O>C1(C)C=C(C)C=C(C)C=1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]1[C:10]2[O:15][CH:27]([CH2:26][OH:29])[CH2:28][C:11]=2[CH:12]=[CH:13][CH:14]=1
Treatment of 2′,6′-difluoro-1,1′-biphenyl-2-ol (3.8 g, 18.43 mmol) with potassium carbonate (10.19 g, 73.72 mmol) and allyl bromide (2.67 g, 22.11 mol), followed by refluxing the resultant allyl ether in mesitylene generally according to the procedure described for Intermediate 8 provided 3-allyl-2′,6′-difluoro-1,1′-biphenyl-2-ol. Treatment of the 3-allyl-2′,6′-difluoro-1,1′-biphenyl-2-ol (3.41 g, 13.85 mmol) with 3-chloroperoxybenzoic acid (7.25 g, 41.54 mmol, 77%) followed by potassium carbonate (4.78 g, 34.62 mmol) generally according to the procedure described for Intermediate 9 afforded 3.5 g (72%) of (±)-[7-(2,6-difluorophenyl)-2,3-dihydro-1-benzofuran-2-yl]methanol as an amber oil. Anal. calcd. for C15H12F2O2: C, 68.7; H, 4.61. Found C, 67.26; H, 4.5.
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