Hydrochloric Acid → 2-(Methoxymethyl)-4-(4-(methylsulfonyl)phenoxy)benzofuran-6-carboxylic acid

HRID 1643757Notes

Reaction equation

Br[CH2:2][C:3]1[O:4][C:5]2[CH:11]=[C:10]([C:12](OCC)=[O:13])[CH:9]=[C:8]([O:17][C:18]3[CH:23]=[CH:22][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:20][CH:19]=3)[C:6]=2[CH:7]=1.[CH3:28][O-:29].[Na+].[OH2:31].Cl>C1COCC1.CO>[CH3:28][O:29][CH2:2][C:3]1[O:4][C:5]2[CH:11]=[C:10]([C:12]([OH:13])=[O:31])[CH:9]=[C:8]([O:17][C:18]3[CH:19]=[CH:20][C:21]([S:24]([CH3:27])(=[O:26])=[O:25])=[CH:22][CH:23]=3)[C:6]=2[CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of ethyl 2-(bromomethyl)-4-(4-(methylsulfonyl)phenoxy)benzofuran-6-carboxylate (285a) (750 mg, 1.65 mmol) in THF and MeOH (3:1, 15 mL) was added NaOMe in MeOH(25% w/w, 1 mL) drop-wise at 0° C. After the solution was stirred at 0° C. for 2 hours, water was added and the stirring was continued for 14 h. The solvents were reduced under reduced pressure. To the aqueous solution was added 1N HCl until the pH ˜1. The product was extracted with CHCl3 and dried over MgSO4. The solution was concentrated to give the title compound (610 mg, 98%) as a white solid. The product was usedin the next step without further purification. 1H NMR (300 MHz, CHLOROFORM-D) δ ppm 3.07 (s, 3 H) 3.46 (s, 3 H) 4.56 (s, 2 H) 6.58 (s, 1 H) 7.07-7.17 (m, 2 H) 7.67 (d, J=1.13 Hz, 1 H) 7.85-7.99 (m, 2 H) 8.13 (d, J=1.13 Hz, 1 H).

Workup

waitthe stirring was continued for 14 h
extractionThe product was extracted with CHCl3
dry with materialdried over MgSO4
concentrationThe solution was concentrated

Sources & evidence

ORD record: ord-36b0206fe7f14f1faefd0ac8164c20d1
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08119624B2

Reaction notes

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