ChemicalBook CAS DataBase List 7-CHLORO-BENZO[B]THIOPHENE

7-CHLORO-BENZO[B]THIOPHENE synthesis

14synthesis methods

Product Name:7-CHLORO-BENZO[B]THIOPHENE
CAS Number:90407-14-0
Molecular formula:C8H5ClS
Molecular Weight:168.64

(2-CHLOROPHENYL)(2,2-DIETHOXYETHYL)SULFANE

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90407-14-0
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Yield:90407-14-0 93%

Reaction Conditions:

with PPA in chlorobenzene; for 25.5 h;Heating / reflux;

Steps:

80.A

EXAMPLE 80[4-(7-Chloro-benzo[b]thiophen-2-yl)-pyrimidin-2-yl]-[3-(4-methyl-piperazin-1-yl)-propyl]-amine; (A). Preparation of 7-chloro-benzo[b]thiopheneInto a 2 L round bottomed flask is added 2-chlorobenzenethiol (50.0 g, 346 mmol), potassium carbonate (52.7 g, 381 mmol) and acetone (1 L). 2-Bromo-1,1-diethoxyethane (71.5 g, 363 mmol) is added and the mixture is heated to reflux for 24 hours. The cooled mixture is filtered and concentrated under reduced pressure to yield crude 2-chlorophenyl-(2,2-diethoxyethyl)sulfane as a pale pink oil (101.8 g, quantitative). A 2 L, 3-necked round-bottomed flask, fitted with a mechanical stirrer, condenser and addition funnel is charged with chlorobenzene (1 L) and polyphosphoric acid (200 g) and the mixture is heated to reflux. At reflux the crude (2-chlorophenyl)(2,2-diethoxyethyl)sulfane is added dropwise over 1.5 hours and the mixture is refluxed for a further 24 hours. The cooled organic layer is decanted and concentrated under reduced pressure. The crude material is subjected to chromatography on silica (hexane) to provide the title compound as a brown oil (54.4 g, 93% yield).

References:

US2008/306082,2008,A1 Location in patent:Page/Page column 26