Methanol → 476199-03-8

HRID 1822961Notes

Reaction equation

[F:1][C:2]1[C:10]2[S:9][C:8]([C:11]([O:13]C)=[O:12])=[CH:7][C:6]=2[C:5]([O:15][CH3:16])=[CH:4][CH:3]=1.[OH-].[Na+].CO>O>[F:1][C:2]1[C:10]2[S:9][C:8]([C:11]([OH:13])=[O:12])=[CH:7][C:6]=2[C:5]([O:15][CH3:16])=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of methyl 7-fluoro-4-methoxy-1-benzothiophene-2-carboxylate (67.2 g, 280 mmol), sodium hydroxide (45 g, 1.12 mol), methanol (800 mL) and water (400 mL) were stirred at ambient overnight. The methanol was evaporated and the mixture cooled to 0° C. Acidified with concentrated hydrochloric acid and stirred for 20 mins. The yellow solid was filtered, washing with water (3×100 mL). Dried under vacuum at 45° C. overnight, over phosphorus pentoxide to give the title compound (61.4 g, 97%); δH (300 MHz, d6-DMSO) 8.10 (1H, d, ArH) 7.44 (1H, t, ArH) 7.00 (1H, m, ArH) and 4.02 (3H, s, OCH3).

Workup

customThe methanol was evaporated
stirringAcidified with concentrated hydrochloric acid and stirred for 20 mins
filtrationThe yellow solid was filtered
washwashing with water (3×100 mL)
dry with materialDried under vacuum at 45° C. overnight, over phosphorus pentoxide

Sources & evidence

ORD record: ord-aaa46bb5ccac49cd935857785ed1c860
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07037932B2

Reaction notes

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