Iodine → 4-Fluoro-7-methoxy-1-benzothiophene-2-carboxylic acid

HRID 2218099Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1/[CH:10]=[C:11](\[SH:15])/[C:12]([OH:14])=[O:13].II.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+].CCOCC>C(COC)OC>[F:1][C:2]1[C:3]2[CH:10]=[C:11]([C:12]([OH:14])=[O:13])[S:15][C:4]=2[C:5]([O:8][CH3:9])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 160 °C

Procedure

(2Z)-3-(2-Fluoro-5-methoxyphenyl)-2-mercapto-2-propenoic acid (1.00 g, 4.38 mmol) was added in one portion to a solution of iodine (1.66 g, 6.56 mmol) in dimethoxyethane (10 mL). This was heated in the microwave with 300 W at 160° C. for 10 mins. After this time the reaction was allowed to cool to room temperature and poured onto saturated sodium metabisulphite (200 mL) and ether (400 mL). Ether layer was separated and product extracted with aqueous sodium hydroxide (2 N, 2×100 mL). This was then acidified to pH 2 with aqueous hydrochloric acid (2 N, 250 mL), and product extracted with ether (2×150 mL). The combined organic extracts were dried (MgSO4) and concentrated in vacuo to give a white solid (580 mg, 30%); δH (300 MHz, CD3OD) 8.00 (1H, s, Ar), 7.30-7.19 (1H, m, Ar), 7.10-7.00 (1H, m, Ar), 3.95.(3H, s, OCH3).

Workup

temperatureto cool to room temperature
customEther layer was separated
extractionproduct extracted with aqueous sodium hydroxide (2 N, 2×100 mL)
extractionextracted with ether (2×150 mL)
dry with materialThe combined organic extracts were dried (MgSO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-b95160f6ca2e4b628726f5148d5c9b0e
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07410982B2

Reaction notes

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