Hydrogen Bromide → 2-Bromo-4-chlorobenzoic acid

HRID 6968

Reaktionsgleichung

Reaktionsgleichung von HRID 6968
[N+]([O-])([O-])=O.[Na+].N[C:7]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10].[BrH:17]>O.[Cu](Br)Br>[Br:17][C:7]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:8]=1[C:9]([OH:11])=[O:10]

Komponenten

6

Edukt 3

HCID 260Hydrogen BromideHCID 24268Sodium NitrateHCID 666462-Amino-4-chlorobenzoic acid

Produkt 1

HCID 331262-Bromo-4-chlorobenzoic acidAusbeute 59 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24611Copper bromide (CuBr2)KatalysatorHCID 962WaterLösungsmittel3×

Versuchsvorschrift

An aqueous solution of sodium nitrate (2.21 g) in water (15 mL) is added dropwise to a stirred, ice-cooled mixture of 2-amino-4-chlorobenzoic acid (5.00 g, 29.1 mmol) and 48% hydrobromic acid (150 mL) in water (150 mL). The resultant mixture is stirred for 2 hr at 0° C. Then it is treated dropwise with an aqueous solution of copper bromide (7.81 g) in water (20 mL). Upon the completion of the addition, the reaction mixture is allowed to warm to ambient temperature where it is stirred overnight. After extraction with ethyl acetate/hexanes (3:1; 2×400 mL), the combined organic layers are washed with brine (200 mL), dried, concentrated, and chromatographed on silica (1% methyl alcohol and 0.5% acetic acid in chloroform) to give the title compound (4.04 g, 59% yield). mp 154–155° C.; ES(−)MS m/z 233, (M−H)− consistent with 1 Br an 1 Cl.

Aufarbeitung

  1. temperaturecooled
  2. additionUpon the completion of the addition
  3. extractionAfter extraction with ethyl acetate/hexanes (3:1; 2×400 mL)
  4. washthe combined organic layers are washed with brine (200 mL)
  5. customdried
  6. concentrationconcentrated
  7. customchromatographed on silica (1% methyl alcohol and 0.5% acetic acid in chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-09dbf5b4d43440c18a10b96ec12ac8d1
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07084170B2

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