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Synthesis of 1,1-dichloroalkanes

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The combination of Ph3P and easily available 1,2-dihaloethanes (XCH2CH2X; X = Cl, Br, or I), was very effective for a mild deoxygenative halogenation of alcohols and aldehydes. The use of (EtO)3P instead of Ph3P enables a convenient purification process, as the byproduct (EtO)3P═O could be removed by aqueous washing. A dehydroxy-fluorination proceeds well in the presence of ICH2CH2I and CsF as fluoride source in DMF.
J. Chen, J.-H. Lin, J.-C. Xiao, Org. Lett., 2018, 20, 3061-3064.


Phthaloyl chloride as reagent and N-formylpyrrolidine as Lewis base catalyst enable a transformation of aldehydes into geminal dichlorides. This simple reaction offers mild reaction conditions, high levels of functional group compatibility, and scalability.
P. H. Huy, Synthesis, 2019, 51, 2474-2483.