Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].P([O-])([O-])([O-])=O.[K+].[K+].[K+].[C:16]([C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1)(=[O:18])[CH3:17].C1COCC1>CCOC(C)=O>[C:16]([C:19]1[CH:24]=[CH:23][C:22]([CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])=[CH:21][CH:20]=1)(=[O:18])[CH3:17]Ethyl bromoacetate (1.70 g, 10.2 mmol), tris-(1-naphthylene)phosphine (379 mg, 0.93 mmol) and tribasic potassium phosphate (10.8 g, 51 mmol) were placed in a flask. The flask was evacuated and back-filled with argon. A solution of 4-acetylphenylboronic acid (2.0 g, 12.2 mmol) in anhyd THF (40 mL) was added to the flask. The reaction was stirred at rt for 16 h. The reaction was diluted with EtOAc, washed with water and brine, dried over MgSO4, filtered and evaporated to dryness. The residue was pre-adsorbed on to SiO2 and the product isolated via SiO2 chromatography to yield 616 mg (29%) of ethyl 4-acetyl-phenylacetate. MS 207.1 (M+H)+.
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