2-CHLORO-5-FLUOROBENZOTHIAZOLE synthesis
- Product Name:2-CHLORO-5-FLUOROBENZOTHIAZOLE
- CAS Number:154327-27-2
- Molecular formula:C7H3ClFNS
- Molecular Weight:187.62
155559-81-2
154327-27-2
General procedure for the synthesis of 2-chloro-5-fluorobenzothiazole from 5-fluoro-2-mercaptobenzothiazole: Thionyl chloride (0.3 mL, 4.41 mmol) was slowly added dropwise to 5-fluoro-2-mercaptobenzothiazole (680 mg, 3.67 mmol). The reaction mixture was stirred at room temperature for 1 h. The reaction was then warmed up to 60 °C and continued for 40 min. Upon completion of the reaction, the reaction solution was cooled to room temperature, slowly poured into ice water and extracted with ethyl acetate (3 x 50 mL). The organic phases were combined, washed with saturated brine and dried over anhydrous sodium sulfate. The dried organic phases were concentrated under reduced pressure to afford the target product 2-chloro-5-fluorobenzothiazole (520 mg, 2.75 mmol, 75% yield).ESI-MS (M + 1): 187 (calculated value: C7H3ClFNS, 186).
155559-81-2
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154327-27-2
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$55.00/250mg
Yield: 75%
Reaction Conditions:
with sulfuryl dichloride at 20 - 60; for 100 h;
Steps:
6.2
Sulfuryl chloride (0.3 mL, 4.41 mmol) was added neat to 5-fluoro-benzothiazole-2-thiol (680 mg, 3.67 mmol). The mixture was stirred at RT for 1 hour, and then heated to 60°C for 40 mins. The resulting solution was cooled to room temperature, and poured onto ice, extracted with EtOAc (3x50 mL), washed with brine and dried over Na2S04. The dried organic layers were concentrated to give 2-chloro-5-fluorobenzo[d]thiazole (520 mg, 2.75 mmol, 75%). ESI-MS (M+l): 187 calc. for C7H5CIFN4S 186.
References:
AMGEN INC.;ALLEN, Jennifer;FROHN, Michael;HARRINGTON, Paul;PICKRELL, Alexander;RZASA, Robert;SHAM, Kelvin;HU, Essa WO2011/143366, 2011, A1 Location in patent:Page/Page column 57
20358-07-0
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154327-27-2
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367-30-6
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154327-27-2
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372-19-0
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154327-27-2
71 suppliers
$55.00/250mg