Dimethyl Sulfoxide → 2-Chloro-6-iodobenzaldehyde
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C(Cl)(=O)C(Cl)=O.CS(C)=O.[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([I:18])[C:13]=1[CH2:19][OH:20].C(N(CC)CC)C>ClCCl.O>[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([I:18])[C:13]=1[CH:19]=[O:20]C(Cl)(=O)C(Cl)=O.CS(C)=O.[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([I:18])[C:13]=1[CH2:19][OH:20].C(N(CC)CC)C>ClCCl.O>[Cl:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([I:18])[C:13]=1[CH:19]=[O:20]
To a solution of 3.11 ml (36.2 mmol) oxalyl chloride in 40 ml dichloromethane at −78° C. was added dropwise over 20 min a solution of 5.14 ml (72.4 mmol) dimethylsulfoxide in 15 ml dichloromethane. The mixture was stirred for a further 15 min at −78° C. and then a solution of 8.10 g (3.02 mmol) (2-chloro-6-iodo-phenyl)-methanol in 40 ml dichloromethane was added dropwise over 30 min and stirring continued at −78° C. for a further 45 min. 20.9 ml (151 mmol) triethylamine were then added dropwise and the reaction mixture allowed to warm to room temperature. Water was then added and the phases were then separated. The organic phase was dried over Na2SO4, filtered and concentrated in vacuo to afford 8.35 g (100%) of the title compound as a yellow crystalline solid which was used in the next step without further purification. MS (EI): 268.0 (44%) & 266.0 (100%) (M+).
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