Dimethyl Sulfoxide → Methyl benzo(b)thiophene-2-carboxylate

A 100 ml 3-necked round-bottomed flask, reflux condenser, thermometer adapter, gas inlet, and Teflon stirrer were oven-dried for 12 hours at 160° C. The apparatus was rapidly assembled, fitted with a thermometer, flushed with dry nitrogen gas, sealed with rubber septa and allowed to cool to room temperature. The cooled reaction flask was charged with anhydrous dimethyl sulfoxide (40 ml), 2-fluorobenzaldehyde (4.44 g, 31.53 mmole), anhydrous triethylamine (2.5 equivalents, 78.83 mmole, 7.976 g, 11 ml) and methyl thioglycolate (1.1 equivalents, 3.681 g, 3.10 ml, 34.68 mmole) and heated to 75° C. with rapid stirring. The progress of the reaction was monitored by TLC (silica, 10% dichloromethane-hexane, UV visualization). After 18 hours the reaction mixture was cooled to room temperature and poured onto an ice/water bath (250 ml). The resulting slurry was stirred for 20 minutes, filtered, washed with cold water (2×100 ml) and dried in vacuo to give 5.136 g (85%) of methyl benzo[b]thiophene-2-carboxylate.

1. temperatureA 100 ml 3-necked round-bottomed flask, reflux condenser, thermometer adapter, gas inlet, and Teflon stirrer
2. customwere oven-dried for 12 hours at 160° C
3. customfitted with a thermometer
4. customflushed with dry nitrogen gas
5. customsealed with rubber septa
6. customThe cooled reaction flask
7. temperatureheated to 75° C. with rapid stirring
8. temperatureAfter 18 hours the reaction mixture was cooled to room temperature
9. additionpoured onto an ice/water bath (250 ml)
10. filtrationfiltered
11. washwashed with cold water (2×100 ml)
12. customdried in vacuo

ORDレコード

ord-514c7e6eb48741a78599d2c06fda833d

出典データセット

uspto-grants-1999_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05863936