Hydrochloric Acid → 3-Bromo-2-(methylthio)benzo[b]thiophene
Reaction equation
Br[C:2]1[S:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[C:3]=1[Br:11].C([Li])CCC.[CH3:17][S:18]SC.Cl>C(OCC)C.CCCCCC>[Br:11][C:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[S:6][C:2]=1[S:18][CH3:17]Participants
Procedure
A solution of 8.76 g of 2,3-dibromobenzo[b]thiophene in 75 ml of diethyl ether was cooled to 0° C. and 19 ml of a 1.6M solution of n-butyl lithium in hexane and 10 ml of diethyl ether were added. A pink slurry formed which was stirred for one hour. A solution of 2.7 ml of methyl disulfide in 10 ml of diethyl ether was added and the reaction mixture was stirred for 4 hours at 0° C. Approximately 100 ml of 1N hydrochloric acid were added and the reaction was allowed to warm to room temperature. The layers were separated and the aqueous layer was extracted with diethyl ether. The combined organic extracts were dried over magnesium sulfate and evaporated to dryness. The resulting oil was vacuum distilled at 1.5 torr providing 1 g of the desired subtitled intermediate.
Workup
- customA pink slurry formed which
- stirringthe reaction mixture was stirred for 4 hours at 0° C
- customThe layers were separated
- extractionthe aqueous layer was extracted with diethyl ether
- dry with materialThe combined organic extracts were dried over magnesium sulfate
- customevaporated to dryness
- distillationdistilled at 1.5 torr
Sources & evidence
- ORD record
- ord-8e012850c99649039112604970465041
- Source dataset
- uspto-grants-1987_04
- Patent number
- US04659717
Reaction notes
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