CHjCl

Methylene chloride CHjCl, b.p. 41°, is obtained as a by product in the com mercial preparation of chloroform by the reduction of carbon tetrachloride with moist iron and also as one of the products in the chlorination of methane it is a useful extraction solvent completely immiscible with water. 

By the action of a dialkyl sulphate upon a Grignard reagent, for example CsH.CHjCl-1-Mg CeH.CHjMgCl C,H,CHjMgCl -1- (C,Hj),SO, — CeHjCH.CH.CH, MgCl(SOAH )... 

Oxidation of side chains. The oxidation of halogenated toluenes and similar compounds and of compounds with side chains of the type —CHjCl and —CH OH proceeds comparatively smoothly with alkaline permanganate solution (for experimental details, see under AromcUic Hydrocarbons, Section IV.9,6 or under Aromatic Ethers, Section IV,106). The resulting acid may be identified by a m.p. determination and by other teats (see Section IV,175). 

Substituted carbenoids such as LiCsC-C(CH3)2CI, are less stable than LiCsC-CHjCl. ... 

A solution of 6-bromoindole (O.lOmol) in toluene (200 ml) was treated with Pd(PPh3)4 (5mol%) and stirred for 30 min. A solution of 4-fluorophenyl-boronic acid (0.25 M, 0.15 mol) in abs. EtOH was added, followed immediately by sal aq. NaHCOj (10 eq.). The biphasic mixture was refluxed for several hours and then cooled to room temperature. The reaction mixture was poured into sat. aq. NaCl (200 ml) and the layers separated. The aq. layer was extracted with additional EtOAc (200 ml) and the combined organic layers dried (Na2S04), filtered and concentrated in vacuo. The solution was filtered through silica gel using hexane-CHjCl -hexanc for elution and evaporated. Final purification by recrystallization gave the product (19 g, 90%). 

H CHjCl H Cl, water, cool, then stand overnight 2.S 221... 

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