C(Cl)Cl.[Br:4][C:5]1[CH:10]=[CH:9][C:8]([CH2:11][C:12]([OH:14])=O)=[CH:7][C:6]=1[O:15][CH3:16].[C:17](Cl)(=O)[C:18](Cl)=O.[Cl-].[Cl-].[Cl-].[Al+3]>CN(C=O)C>[Br:4][C:5]1[CH:10]=[C:9]2[C:8](=[CH:7][C:6]=1[O:15][CH3:16])[CH2:11][C:12](=[O:14])[CH2:18][CH2:17]2To a DCM solution of (4-Bromo-3-methoxyphenyl)acetic acid (900 mg, 3.67 mmol) was added oxalyl chloride (0.64 ml, 7.3 mmol) and a drop of DMF. The solution was allowed to stir at RT for 3 hours, at which point bubbling stopped. The volatiles were removed under vacuum, and the residue was redissolved in DCM. The solution was cooled to 0° C. To this solution was added aluminum trichloride (1.2 g, 9.2 mmol). After stirring the mixture for 15 minutes, ethylene was bubbled into the reaction. The reaction was poured into ice, extracted with DCM, washed with brine, and purified by MPLC. LC-MS (IE, m/z): 255 [M+1]+.
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