Triethylamine → Methyl 7-fluoro-4-methoxy-1-benzothiophene-2-carboxylate

HRID 1822960Notes

Reaction equation

[C:1]([O:5][CH3:6])(=[O:4])[CH2:2][SH:3].C(N(CC)CC)C.F[C:15]1[C:22]([F:23])=[CH:21][CH:20]=[C:19]([O:24][CH3:25])[C:16]=1[CH:17]=O>CN(C)C=O>[F:23][C:22]1[C:15]2[S:3][C:2]([C:1]([O:5][CH3:6])=[O:4])=[CH:17][C:16]=2[C:19]([O:24][CH3:25])=[CH:20][CH:21]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Methyl thioglycolate (28.8 mL, 320 mmol) was added under nitrogen to a solution of triethylamine (86.6 mL) in dry N,N-dimethylformamide (220 mL) at 80° C. Stirred at 100° C. for 15 mins. A solution of 2,3-difluoro-6-methoxybenzaldehyde (55.1 g, 320 mmol) in N,N-dimethylformamide (80 mL) was added and the mixture heated at 130° C. for 3 h. Allowed to cool then poured onto ice-water (2 L). The resulting yellow solid was filtered, washing with water (2×200 mL). Dried under vacuum over phosphorus pentoxide at room temperature overnight to give the title compound (67.2 g, 87%); δH (300 MHz, CDCl3) 8.20 (1H, d, ArH), 7.06 (1H, t, ArH), 6.68 (1H, m, ArH) and 3.99 (6H, s, OCH3 and CO2CH3).

Workup

temperaturethe mixture heated at 130° C. for 3 h
temperatureAllowed to cool
additionthen poured onto ice-water (2 L)
filtrationThe resulting yellow solid was filtered
washwashing with water (2×200 mL)
dry with materialDried under vacuum over phosphorus pentoxide at room temperature overnight

Sources & evidence

ORD record: ord-a8c340c7c4ff40b1a127da3aaa232f14
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07037932B2

Reaction notes

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