Br[C:2]1[CH:14]=[CH:13][C:5]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])=[CH:4][C:3]=1[O:15][CH3:16].[CH3:17][O:18][C:19]([O:23][Si](C)(C)C)=[C:20]([CH3:22])[CH3:21]>CN(C=O)C.[F-].[F-].[Zn+2]>[CH3:16][O:15][C:3]1[CH:4]=[C:5]([CH:13]=[CH:14][C:2]=1[C:20]([CH3:22])([CH3:21])[C:19]([O:18][CH3:17])=[O:23])[C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7]To a microwave vial was added ZnF2 (36 mg, 0.35 mmol) and Pd(tBu3P)2 (7.2 mg, 0.014 mmol). The reaction vessel was purged with nitrogen for 10 minutes before tert-butyl 4-bromo-3-methoxy-benzoate (200 mg, 0.70 mmol) dissolved in DMF (2.5 mL) was added followed by (1-methoxy-2-methyl-prop-1-enoxy)-trimethyl-silane (180 mg, 1.1 mmol). The reaction vessel was placed in an 80° C. oil bath under an atmosphere of nitrogen and the mixture was allowed to stir overnight. The mixture was allowed to cool to rt and was filtered through a frit and was washed with brine and EtOAc. The organics were separated and dried over sodium sulfate. The solvent was removed and the residue was taken on to the next step without additional purification. ESI-MS m/z calc. 308.2, found 309.4 (M+1)+; Retention time: 3.12 minutes (4 min run).
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