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

HRID 713736

Reaction equation

HRID 713736 reaction equation
[H-].[Na+].[F:3][C:4]([F:8])([F:7])[CH2:5][OH:6].C[O:10][C:11]([C:13]1[O:14][C:15]2[CH:23]=[CH:22][CH:21]=[CH:20][C:16]=2[C:17]=1[CH2:18]Br)=[O:12].[OH-].[Na+].Cl>CN(C=O)C>[F:3][C:4]([F:8])([F:7])[CH2:5][O:6][CH2:18][C:17]1[C:16]2[CH:20]=[CH:21][CH:22]=[CH:23][C:15]=2[O:14][C:13]=1[C:11]([OH:12])=[O:10]

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

Sodium hydride (15 mg, 0.56 mmol) was suspended in anhydrous DMF and stirred under N2(g). 2,2,2-Trifluoroethanol (270 μL, 3.7 mmol) was added and after stirring the reaction mixture for 15-20 min., 3-bromomethylbenzofuran-2-carboxylic acid methyl ester was added. After 8 h, 1N NaOH (aq.) was added and the reaction mixture was stirred for 10-15 min. The reaction mixture was acidified reaction to pH 3 with aqueous hydrochloric acid and the product was extracted with EtOAc. The organic layer was dried organic over Na2SO4 and concentrated in vacuo to give 3-(2,2,2-trifluoroethoxymethyl)benzofuran-2-carboxylic acid (38 mg) which was then used without purification.

Workup

  1. stirringafter stirring the reaction mixture for 15-20 min.
  2. stirringthe reaction mixture was stirred for 10-15 min
  3. extractionthe product was extracted with EtOAc
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0b81eb893faa4199a158c8e195a94d9e
Source dataset
uspto-grants-2015_11
Patent number
US09186347B1

Linked notes

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