Methanol → 4-Bromo-2-tert-butyl-5-phenyl-1-benzofuran-7-carboxylic Acid

HRID 17543Notes

Reaction equation

HRID 17543 reaction equation
CO.[OH-].[K+].[Br:5][C:6]1[C:11]2[CH:12]=[C:13]([C:15]([CH3:18])([CH3:17])[CH3:16])[O:14][C:10]=2[C:9]([C:19]([O:21]C)=[O:20])=[CH:8][C:7]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>O1CCCC1>[Br:5][C:6]1[C:11]2[CH:12]=[C:13]([C:15]([CH3:17])([CH3:18])[CH3:16])[O:14][C:10]=2[C:9]([C:19]([OH:21])=[O:20])=[CH:8][C:7]=1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 68584682Methyl 4-bromo-2-tert-butyl-5-phenyl-1-benzofuran-7-carboxylate

Product 1

HCID 685849474-Bromo-2-tert-butyl-5-phenyl-1-benzofuran-7-carboxylic AcidYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A methanol (12 ml) solution of potassium hydroxide (1.26 g, 22.5 mol) was put into a tetrahydrofuran (50 ml) solution of methyl 4-bromo-2-tert-butyl-5-phenyl-1-benzofuran-7-carboxylate (I-255) (2.90 g, 7.49 mmol), followed by stirring at room temperature for 3.5 hours. The reaction liquid was concentrated under reduced pressure, then 1 N hydrochloric acid (100 ml) and water (100 ml) were added, the product was extracted with ethyl acetate (200 ml×2). The organic layer was washed with saturated brine (50 ml×2), then dried over anhydrous magnesium sulfate, concentrated under reduced pressure to obtain the entitled compound (2.64 g, 95%) as a yellow white solid.

Workup

  1. customThe reaction liquid
  2. concentrationwas concentrated under reduced pressure
  3. addition1 N hydrochloric acid (100 ml) and water (100 ml) were added
  4. extractionthe product was extracted with ethyl acetate (200 ml×2)
  5. washThe organic layer was washed with saturated brine (50 ml×2)
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4e81da8c260d410aa8bfa1025a4fbfe9
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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