Succinic anhydride → 4-(4-Bromo-2-methylphenyl)-4-oxobutanoic acid

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5](I)=[C:4]([CH3:9])[CH:3]=1.C([Mg]Br)(C)C.[C:15]1(=[O:21])[O:20][C:18](=[O:19])[CH2:17][CH2:16]1>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:15](=[O:21])[CH2:16][CH2:17][C:18]([OH:20])=[O:19])=[C:4]([CH3:9])[CH:3]=1

Participants

Procedure

To a solution of 4-bromo-1-iodo-2-methylbenzene (148 mg, 0.5 mmol) in THF (10 mL) at −25° C. was added isopropylmagnesium bromide (0.5 mL, 0.5 mmol) and stirred 3 h. Succinic anhydride (55 mg, 0.55 mmol) was added and the reaction was stirred 18 h. The mixture was quenched with water (10 mL) and washed with 1N NaOH (10 mL), 1N HCl (10 mL), brine (10 mL) and dried (MgSO4). The organic layer was concentrated in vacuo and the residue purified by flash chromatography (0-100% EtOAc/Hexane) to afford 55A (42 mg, 31%) as a crystalline solid. 1H NMR (400 MHz, CDCl3) δ ppm 0.98 (t, 3 H) 2.42 (q, 2 H) 2.73 (t, 2 H) 4.10 (t, 2 H) 6.82 (d, 1 H) 7.02 (d, 1 H) 7.09 (t, 2 H) 7.15 (t, 1 H) 7.36 (d, 1 H) 7.58-7.63 (m, 1 H).