Boron tribromide → 2-(3-hydroxyphenyl)benzoic Acid

HRID 278167Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 278167
C[O:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=2[C:11]([OH:13])=[O:12])[CH:6]=[CH:7][CH:8]=1.B(Br)(Br)Br>C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=2[C:11]([OH:13])=[O:12])[CH:6]=[CH:7][CH:8]=1

Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 27595492-(3-methoxyphenyl)benzoic Acid

Produkt 1

HCID 27593002-(3-hydroxyphenyl)benzoic Acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

2-(3-Methoxyphenyl)benzoic acid from Step B (6.53 g, 28.6 mmol) was dissolved in dry CH2Cl2 (100 mL) under argon and cooled to −78° C. Boron tribromide (62.9 mL of a 1.0 M solution in CH2Cl2, 62.9 mmol) was added dropwise and the solution was stirred overnight and allowed to warm slowly to ambient temperature. The resulting mixture was cooled in an ice bath and quenched carefully with water (200 mL), then extracted with CH2Cl2 (3×250 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated under reduced pressure to give the titled product which was sufficiently pure for use in the next step.

Aufarbeitung

  1. temperatureto warm slowly to ambient temperature
  2. temperatureThe resulting mixture was cooled in an ice bath
  3. customquenched carefully with water (200 mL)
  4. extractionextracted with CH2Cl2 (3×250 mL)
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-1998b0214d95455ea5bf5ae5fac151e2
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06358985B1

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