[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[CH3:9].[F:10][CH2:11][CH2:12]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1.CCOC(C)=O.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:12][CH2:11][F:10])=[CH:4][C:3]=1[CH3:9]
A solution of 4-bromo-3-methyl-phenol (3.74 g, 20 mmol), 2-fluoro-ethanol (2.29 mL, 22 mmol), and triphenylphosphine (5.77 g, 22 mmol) in dry THF (15 mL) was cooled to 0° C. under stirring. Diethyl azodicarboxylate (40% in toluene, 10 mL, 22 mmol) was added and the reaction mixture was allowed to come to RT overnight. After 18 h at RT the reaction mixture was poured into a mixture of EtOAc/water. The aqueous phase was extracted with more EtOAc. The organic phases were combined, dried (MgSO4), filtered, and concentrated in vacuo to afford the crude product. The crude product was purified by chromatography eluting with DCM/petroleum ether 1:6 to afford the title compound as colourless oil.
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