Hydrochloric Acid → 3-(2,2,2-Trifluoroethoxymethyl)benzofuran-2-carboxylic acid

HRID 2221437Notes

Reaction equation

HRID 2221437 reaction equation
[H-].[Na+].[F:3][C:4]([F:8])([F:7])[CH2:5][OH:6].Br[CH2:10][C:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[O:13][C:12]=1[C:20]([O:22]C)=[O:21].[OH-].[Na+].Cl>CN(C=O)C>[F:3][C:4]([F:8])([F:7])[CH2:5][O:6][CH2:10][C:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[O:13][C:12]=1[C:20]([OH:22])=[O:21]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 64092,2,2-TrifluoroethanolHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 100838Methyl 3-(bromomethyl)-2-benzofurancarboxylate

Product 1

HCID 289432073-(2,2,2-Trifluoroethoxymethyl)benzofuran-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (15 mg, 0.56 mmol) in anhydrous DMF (3 ml) was added 2,2,2-trifluoroethanol (270 μL, 3.7 mmol). The reaction mixture was stirred for 15-20 min and methyl 3-bromomethylbenzofuran-2-carboxylate (prepared as described in Reference C below) was added. Stirring was continued for 8 h, 1N aqueous NaOH was added and the reaction mixture was stirred for additional 10-15 min. The reaction mixture was acidified with 3M aqueous HCl to pH 3 and the product was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated in vacuo to give crude 3-(2,2,2-trifluoroethoxymethyl)benzofuran-2-carboxylic acid (38 mg, 0.139 mmol), which was used without further purification.

Workup

  1. stirringStirring
  2. waitwas continued for 8 h
  3. stirringthe reaction mixture was stirred for additional 10-15 min
  4. extractionthe product was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5588b112ed81469c923186acc0ecf73b
Source dataset
uspto-grants-2008_05
Patent number
US07368572B2

Reaction notes

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