FC1C=CC=C(F)C=1O.C([O-])([O-])=O.[K+].[K+].BrCC([O-])=O.C([O:23][C:24](=[O:35])[CH2:25][O:26][C:27]1[C:32]([F:33])=[CH:31][CH:30]=[CH:29][C:28]=1[F:34])C.[OH-].[Na+]>CC(C)=O.C(O)C.O>[F:33][C:32]1[CH:31]=[CH:30][CH:29]=[C:28]([F:34])[C:27]=1[O:26][CH2:25][C:24]([OH:35])=[O:23]
2,6-Difluoro-phenol (10.0 g, 92.47 mmol) was dissolved in 15.0 mL of acetone, K2CO3 (7.40 g, 92.47 mmol) and α-bromoacetate (15.44 g, 10.25 mL, 231.18 mmol) were added and the reaction was allowed to reflux overnight. The mixture was filtered through a plug of cotton and the solvent removed in vacuo to give 18.93 g as a colorless oil, 98% yield. 1H NMR (400 MHz, CDCl3): σ 1.26 (t, J=m Hz, 3H), 2.29 (s, 3H), 4.24 (q, J=Hz, 2H), 4.61 (s, 2H), 6.64 (d, J=Hz, 1H), 6.83 (t, J=Hz, 1H), 7.16 (q, J=Hz, 2H) 13C NMR (CDCl3): 169.37, 156.36, 131.13, 127.51, 126.91, 121.63, 111.43, 65.90, 61.41, 16.39, and 14.34. (2,6-Difluoro-phenoxy)-acetic acid ethyl ester (1.66 g) was dissolved in ethanol (10.0 mL), NaOH (2 eqv's) and 5 drops of H2O was added and the reaction stirred at room temperature overnight. The product was filtered and dried to give a white solid, 1.11 g, 64% yield. 1H NMR (400 MHz, d-DMSO): σ 4.84 (s, 2H), 7.31 (m, 1H), 7.46 (m, 1H), 7.93 (m, 1H), 13.19 (s, 1H)
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