Methanol → 476199-03-8

HRID 2220307Notes

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-641be7131acf4ab9b2456b4687512741
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07417064B2

Reaction notes

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