Hypophosphoric acid → Methyl 3-bromo-5-methoxybenzoate

HRID 495979

Reaktionsgleichung

Reaktionsgleichung von HRID 495979
[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([O:13][CH3:14])[C:11]=1N)[C:5]([O:7][CH3:8])=[O:6].N([O-])=O.[Na+].P(P(O)(O)=O)(O)(O)=O>C(O)C.S(=O)(=O)(O)O.C(O)(=O)C.O>[Br:1][C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([O:13][CH3:14])[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Komponenten

8

Edukt 3

HCID 24536Hypophosphoric acidHCID 22324265Methyl 4-amino-3-bromo-5-methoxybenzoateHCID 23668193Sodium Nitrite

Produkt 1

HCID 15618226Methyl 3-bromo-5-methoxybenzoateAusbeute 100,2 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 176Acetic AcidLösungsmittelHCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel2×HCID 1118Sulfuric AcidLösungsmittel

Versuchsvorschrift

A 500 ml round bottom flask fitted with overhead stirring was charged with 16.5 grams (55 mmole) of methyl 3-bromo-5-methoxy-4-aminobenzoate in 80 ml ethanol, 15 ml sulfuric acid and 20 ml acetic acid. The solution was chilled in an ice bath and 6.6 gms (95 mmole) of sodium nitrite in 30 ml water was added dropwise while maintaining the temperature below 10° C. After stirring an additional 25 minutes, 100 ml of 50% hypophosphoric acid was added and the mixture was stirred cold for 2 hours. The reaction mixture was diluted with 500 ml water, extracted with ether, and then evaporated under reduced pressure to give 13.5 grams of methyl 3-bromo-5-methoxybenzoate as a reddish oil.

Aufarbeitung

  1. customA 500 ml round bottom flask fitted with overhead
  2. temperatureThe solution was chilled in an ice bath
  3. temperaturewhile maintaining the temperature below 10° C
  4. stirringAfter stirring an additional 25 minutes
  5. stirringthe mixture was stirred cold for 2 hours
  6. extractionextracted with ether
  7. customevaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-fa90fa7b37da4b90a2a2326e63d108da
Quelldatensatz
uspto-grants-2005_09
Patentnummer
US06943169B2

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