Methyl chloroacetate → 6-Bromo-1-benzofuran-2-carboxylic acid

HRID 2179563

Reaktionsgleichung

Reaktionsgleichung von HRID 2179563
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4]([OH:10])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:18][C:19]([O:21]C)=[O:20].[OH-].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O.C1COCC1>[Br:1][C:2]1[CH:9]=[CH:8][C:5]2[CH:6]=[C:18]([C:19]([OH:21])=[O:20])[O:10][C:4]=2[CH:3]=1

Komponenten

8

Edukt 4

HCID 7295Methyl chloroacetateHCID 11430Potassium CarbonateHCID 14797Potassium HydroxideHCID 40660194-Bromo-2-hydroxybenzaldehyde

Produkt 1

HCID 14744716-Bromo-1-benzofuran-2-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

8.0 g (39.8 mmol) of 4-bromo-2-hydroxybenzaldehyde and 1.47 g (3.98 mmol) of tetra-n-butylammonium iodide are mixed with 22 g (159.19 mmol) of anhydrous potassium carbonate. 9.07 g (83.57 mmol) of methyl chloroacetate are added. The reaction mixture is heated at 130° C. for 4 h and then cooled to 0° C. in an ice bath. 100 ml of THF and a solution of 13.4 g (238.8 mmol) of potassium hydroxide in 50 ml of water are added, and the mixture is then stirred at RT overnight. The THF is removed under reduced pressure. The remaining aqueous phase is diluted with water and acidified with conc. hydrochloric acid. The precipitated product is filtered off and dried under high vacuum. Silica gel 60 (Merck, Darmstadt; eluent: toluene, toluene/acetic acid 50:1, toluene/acetic acid/methyl acetate 35:1:5) is used for final purification. The solvent is removed under reduced pressure. Finally, the last residues of solvent are removed under high vacuum. 3.8 g (40% of theory) of the title compound are isolated.

Aufarbeitung

  1. temperaturecooled to 0° C. in an ice bath
  2. customThe THF is removed under reduced pressure
  3. additionThe remaining aqueous phase is diluted with water
  4. filtrationThe precipitated product is filtered off
  5. customdried under high vacuum
  6. custompurification
  7. customThe solvent is removed under reduced pressure
  8. customFinally, the last residues of solvent are removed under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-e730d94359344795b53cd62e55ce6292
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09067931B2

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