Hydrochloric Acid → 5-Fluoro-2,3-dihydro-1-benzofuran-2-carboxylic acid
Reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]([CH2:10][OH:11])[CH2:7][C:6]=2[CH:12]=1.C(=O)(O)[O-:14].[K+].[O-]Cl.[Na+].Cl>C(#N)C.O.CC1(C)N([O])C(C)(C)CCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]([C:10]([OH:14])=[O:11])[CH2:7][C:6]=2[CH:12]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 0 °C
Procedure
To a 500 ml round-bottomed flask that contained a solution of (5-fluoro-2,3-dihydro-benzofuran-2-yl)-methanol (3.0 g, 17.8 mmol) in 100 ml of acetonitrile was added a solution of potassium bicarbonate (7.14 g, 71.4 mmol, 4 eq) in 30 ml of water. The mixture was cooled to 0° C. and TEMPO (56 mg, 0.36 mmol, 2 mol %) was added, followed by the dropwise addition of NaOCl(aq) (60 ml, 1.1 eq). The mixture was then stirred for 1.5 hours at room temperature. The pH was then adjusted to 4 using aqueous hydrogen chloride (3N). The mixture was then extracted with 3×80 ml of ethyl acetate. The organic fractions were combined, dried over magnesium sulfate, filtered and then concentrated under vacuum to provide 2.0 grams of the crude product as a yellow solid.
Workup
- customTo a 500 ml round-bottomed flask that contained
- extractionThe mixture was then extracted with 3×80 ml of ethyl acetate
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-dd33cd9ab04f4760be068a0441b42a93
- Source dataset
- uspto-grants-2016_02
- Patent number
- US09249102B2
Reaction notes
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