Lithium hydroxide, monohydrate → HCID 67393208, compound

HRID 1776938Notes

Reaction equation

[Br:1][C:2]1[C:3]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=3)=[C:7]([C:17]([O:19]CC)=[O:18])[C:6]=2[CH:22]=1.O[Li].O>O1CCOCC1.O>[Br:1][C:2]1[C:3]([NH:23][S:24]([CH3:27])(=[O:25])=[O:26])=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=3)=[C:7]([C:17]([OH:19])=[O:18])[C:6]=2[CH:22]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of ethyl 5-bromo-2-(4-fluorophenyl)-6-(methylsulfonamido)benzofuran-3-carboxylate (53 g, 0.23 mol) in dioxane/H2O (5/1, 600 mL) was added LiOH.H2O (25 g, 1.17 mol), and the mixture was stirred at 100° C. for 3 hours. After concentrated, the resulting residue was dissolved in H2O, 1 N HCl was added until pH reached 3, and the mixture was extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and filtered. The solvent was removed to provide the product of 5-bromo-2-(4-fluorophenyl)-6-(methylsulfonamido)benzofuran-3-carboxylic acid (48 g, yield: 96%). 1H-NMR (DMSO-d6, 400 MHz) δ 13.49 (s, 1H), 9.67 (s, 1H), 8.30 (s, 1H), 8.12˜8.17 (m, 2H), 7.87 (s, 1H), 7.45˜7.50 (m, 2H), 3.16 (s, 3H). MS (M+H)+: 428/430.

Workup

concentrationAfter concentrated
dissolutionthe resulting residue was dissolved in H2O
addition1 N HCl was added until pH
extractionthe mixture was extracted with EtOAc
washThe organic layer was washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
customThe solvent was removed

Sources & evidence

ORD record: ord-29b44f24f2974894b64b885764288f5b
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09265773B2

Reaction notes

Loading…