[F:1][C:2]1[CH:18]=[CH:17][C:5]2[S:6][C:7]3[CH:14]=[C:13]([CH2:15][OH:16])[CH:12]=[CH:11][C:8]=3[CH:9]=[CH:10][C:4]=2[CH:3]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.C(OCC)(=O)C>C(Cl)Cl.C1(C)C=CC=CC=1>[F:1][C:2]1[CH:18]=[CH:17][C:5]2[S:6][C:7]3[CH:14]=[C:13]([CH:15]=[O:16])[CH:12]=[CH:11][C:8]=3[CH:9]=[CH:10][C:4]=2[CH:3]=1Dissolve 568 mg (2.2 mmole) of 2-fluoro-7-hydroxymethyldibenzo[b,f]thiepin in 30 ml of methylene chloride and add 647 mg of 98% pyridinium chlorochromate. Stir the mixture and follow the reaction by thin layer chromatography (Merck silica gel F254 with 5% ethyl acetate in toluene). When complete, filter the mixture through a bed of Florisil, and wash through with methylene chloride. Evaporate the filtrate to obtain a brown solid (600 mg). Purify the crude product by chromatography on silica gel using totluene as solvent to obtain the title compound as a yellow solid, m.p. 137°-139° C.
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