[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:14]=[CH:13][C:11](N)=[CH:10][CH:9]=2)=[C:4]([O:15][CH3:16])[CH:3]=1.C(O)(=[O:19])C.N([O-])=O.[Na+].S(=O)(=O)(O)O>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:14]=[CH:13][C:11]([OH:19])=[CH:10][CH:9]=2)=[C:4]([O:15][CH3:16])[CH:3]=1A solution of 32.00 grams of 4-(4'-fluoro-2'-methoxyphenyl)-aniline in 120 ml. of glacial acetic acid is cooled to 10° - 12° C. To this solution is added slowly a solution of 12.25 grams of sodium nitrite in 120 ml. of water with stirring and continued cooling. Five minutes after this addition, the suspension of the diazonium acetate is added slowly to a boiling solution of 100 ml. of concentrated sulfuric acid and 200 ml. of water. After the final addition of the diazonium salt, the suspension is boiled for an additional 5 minutes and then allowed to cool to room temperature. The reaction mixture is then filtered and the cake dried in vacuo to yield 4-(4'-fluoro-2'-methoxyphenyl)-phenol.
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