5-(Chlorosulphonyl)-2-fluorobenzoic acid

(1a) 2. Synthesis of Starting Material 21 or 21-1; The intensive trouble-shooting of the 4-step sequence from 2-fluorobenzoic acid (17) to 21 succeeded in an overall yield improvement from 17 to 50percent. The main enhancement was achieved by optimizing the reaction conditions to 19 with sodium sulfite followed by the alkylation reaction with RTo a 500mL three-mouthed flask was added 50mL of chlorosulfonic acid and a stirred, and cooled to 0 deg. C, was added portionwise 18g 2-fluorobenzoic acid was slowly warmed to 75 deg. C, heated overnight, after which the reaction cooled to room temperature, with the stirring was poured into 400mL ice water, a large number of yellow solid was filtered, the cake washed with 30mL toluene and water 3 times. And dried in vacuo to give a yellow solid 22.6g. It was used directly in the next step, yield: 73percent.416g of chlorosulfonic acid was added to a 1000ml reaction flask and cooled to below 0°C with iced saline.Stir and add 100g (0.71mol) of o-fluorobenzoic acid in portions; heat with oil bath, heat to 75°C, stir for 5 hours; cool to room temperature, drop the reaction into 300g ice, produce a white solid, filter, wash, Drying gave 123 g of a white solid, yield 72.2percent.To chlorosulfonic acid (23.8 mL, 350 mmol) cooled to 0 °C was added portionwise 2-fluorobenzoic acid (5 g, 35 mmol). After complete addition, the yellow solution was allowed to warm to room temperature, then heated to 75 °C overnight. The reaction mixture was cooled to room temperature and then added dropwise to ice- water (150 mL). The white precipitate was filtered, washed with water, and dried in vacuo to afford the desired product B02 as a white solid (3.37 g, 40.4 percent).5-(N-((1-Cyclopropyl-1H-1, 2, 3-triazol-4-yl)methyl)sulfamoyl)-N-(3, 4- difluorophenyl)-2-fluorobenzamide (13) 2-fluorobenzoic acid 9 (10.0 g, 71.4 mmol) was added to chlorosulfonic acid (50 mL) at 0 °C and the mixture was stirred at 0 °C for 1 h. The reaction mixture was then slowly poured onto ice. The precipitate formed was filtered, rinsed off with water (3 x 100 mL) and dried under vacuum overnight to yield 5-(chlorosulfonyl)-2- fluorobenzoic acid 10 as a brownish solid (10.5 g, 44.0 mmol). 5-(chlorosulfonyl)-2- fluorobenzoic acid 10 (10.0 g, 41.9 mmol) was added to 60 mL of SOCl

Molecular Weight:238.62
XLogP3:1.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:2
Exact Mass:237.9502856
Monoisotopic Mass:237.9502856
Topological Polar Surface Area:79.8
Heavy Atom Count:14
Complexity:323
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes