NJV-dimethylformamide

The reaction of 1,3,5-tribromobenzene with excess sodium methoxide in methanol—NJV-dimethylformamide and in the presence of a catalytic amount of cuprous iodide gives ca 90% yield phloroglucinol trimethyl ether (1,3,5-trimethoxybenzene). The latter is hydrolyzed with 35 wt % hydrochloric acid at room temperature to give a 90% yield of phloroglucinol (140—142). 

However, there are many molecules where rotation around a particular single bond is restricted, that is, prevented from rotating freely. If rotation is much slower than the NMR time scale, the molecule is essentially locked in one conformation. One example of such a compound is NJV-dimethylformamide (DMF, 10-1), whose NMR data are given in Table 8.1 ... 

A practical disadvantage from the use of NJV-dimethylformamide, methyl sulfoxide, and hexamethylphosphoric triamide is that isolation of the product is sometimes complicated by the necessity of removing these high-boiling solvents (especially hexamethylphosphoric triamide) and, where a facile displacement is involved (as with most primary sulfonates), the use of such lower-boiling, aprotic solvents as acetone, butanone, or acetonitrile may be advantageous. 

Meanwhile, dissolve 10-20 mg of AEC in 0.5 ml of NJV-dimethylformamide in a glass container, then gradually add 50 ml of acetate buffer with constant mixing, add 25 ml of 100-volume H2O2, mix, and filter onto the slides. Incubate for 5-15 min under microscopic control. 

In an initial step the reactive formylating agent is formed from N,N-dimethylformamide (DMF) 2 and phosphorus oxychloride. Other NJV-disubstituted formamides have also found application for example M-methyl-iV-phenylformamide is often used. The formylating agent is likely to be a chloromethyl iminium salt 4—also called the Vilsmeier complex (however its actual structure is not rigorously known)—that acts as the electrophile in an electrophilic substitution reaction with the aromatic substrate 1 (see also Friedel-Crafts acylation reaction) ... 

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