Hydrochloric Acid → HCID 71295150, compound

HRID 1776904Notes

Reaction equation

HRID 1776904 reaction equation
[Br:1][C:2]1[C:3]([NH:24][S:25]([CH3:28])(=[O:27])=[O:26])=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=3[F:17])=[C:7]([C:18]([O:20]CC)=[O:19])[C:6]=2[CH:23]=1.[Li+].[OH-].Cl>O1CCOCC1.O>[Br:1][C:2]1[C:3]([NH:24][S:25]([CH3:28])(=[O:26])=[O:27])=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=3[F:17])=[C:7]([C:18]([OH:20])=[O:19])[C:6]=2[CH:23]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 71295285HCID 71295285, compound

Product 1

HCID 71295150HCID 71295150, compoundYield 71.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of ethyl 5-bromo-2-(2,4-difluorophenyl)-6-(methylsulfonamido)benzofuran-3-carboxylate (653 mg, 1.38 mmol) in 1,4-Dioxane (10 mL) and H2O (1 mL) was added LiOH (289 mg, 6.88 mmol), then the mixture was stirred at 110° C. After 3 hours, 10% HCl (aq) was added until pH reach 4. The mixture was extracted with EtOAc. The organic layer was dried over Na2SO4 and concentrated to provide 5-bromo-2-(2,4-difluorophenyl)-6-(methylsulfonamido)benzofuran-3-carboxylic acid (440 mg, yield: 65%). 1H-NMR (CDCl3, 400 MHz) δ 8.38 (s, 1H), 7.94 (s, 1H), 7.66˜7.94 (m, 1H), 7.08 (d, J=3.0 Hz, 1H), 6.91 (s, 1H), 3.04 (s, 3H). MS (M+H)+: 446/448.

Workup

  1. extractionThe mixture was extracted with EtOAc
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-fa576bc381ee468da018828d88d113d1
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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