Water → Ethyl 6-fluorobenzofuran-3-carboxylate

HRID 1929095Notes

Reaction equation

HRID 1929095 reaction equation
C(OC([C:6]1[O:7][C:8]2[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:9]=2[C:10]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12])=O)C.[Cl-].[Na+].O>CS(C)=O>[CH2:14]([O:13][C:11]([C:10]1[C:9]2[CH:16]=[CH:17][C:18]([F:20])=[CH:19][C:8]=2[O:7][CH:6]=1)=[O:12])[CH3:15]

Participants

5

Reactant 3

HCID 962WaterHCID 5234Sodium ChlorideHCID 668416156-Fluoro-benzofuran-2,3-dicarboxylic acid diethyl ester

Product 1

HCID 66841592Ethyl 6-fluorobenzofuran-3-carboxylateYield 49.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
160 °C

Procedure

109 (40 g, 142.7 mmol) is dissolved in 300 ml of a DMSO and after addition of sodium chloride (16.7 g, 285.4 mmol) and water (5.1 ml) the mixture is stirred for 4 h at 160° C. (temperature of reaction mixture). Then the mixture is allowed to cool down and evaporated at high vacuum. The residue is dissolved in ethyl acetate, washed with water and brine and dried over sodium sulfate. Evaporation gave 14.8 g of an red oil, which is further purified by filtration over silica gel (ethyl acetate/hexanes 2:8).

Workup

  1. custom(temperature of reaction mixture)
  2. temperatureto cool down
  3. customevaporated at high vacuum
  4. dissolutionThe residue is dissolved in ethyl acetate
  5. washwashed with water and brine
  6. dry with materialdried over sodium sulfate
  7. customEvaporation

Sources & evidence

ORD record
ord-6bc96b8f72ed41a28052223b09229e9d
Source dataset
uspto-grants-2012_05
Patent number
US08183366B2

Reaction notes

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