Diethyl Ether → 3-(2-Bromoethyl)indole

Participants

Reaction Steps

The starting materials of formula II in which X1 is mercapto, --S--SO3Na or --S--SO3K, and R2, R3, R4, R5, R6 and R7 are as defined in the first instance are obtained by the following process: The appropriate compound of formula 11 (X1 =OH) described above, is treated with phosphorus tribromide in an inert solvent, for example, ether or methylene chloride to afford the corresponding 3-(2-bromoethyl)-indole derivative. The latter compound is then converted to the desired starting material of formula II (X1 = SH) by a procedure similar to that described by N. N. Suvorov and V. N. Buyanov, Khim.-Farm. Zh., 1, (1967), [Chem. Abstr. 67, 73474a (1967)], for converting 3-(2-bromoethyl)-indole to indole-3-ethanethiol (II; R2, R3,R4, R5 and R6 = H and X1 = SH). Accordingly, the appropriate 3-(2-bromoethyl)-indole derivative is treated with sodium or potassium thiosulfate to afford the corresponding sodium or potassium β-(3-indoly)ethyl thiosulfate derivative, respectively; namely the desired starting materials of formula II (X=--S--SO3Na or --S--SO3K). Treatment of the latter product with strong alkali, for example, sodium or potassium hydroxide, yields the corresponding bis[ω-(3-indolyl)ethyl]-disulfide derivative. Reduction of the latter compound with lithium aluminum hydride gives the desired compounds of formula II (X1 = SH).

Provenance & Evidence