Triethylamine → 2-Hydroxy-3-bromo-4-chloro-5-(1,1-dimethylethyl)benzonitrile

HRID 1710003Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1710003
[OH:1][C:2]1[C:10]([Br:11])=[C:9]([Cl:12])[C:8]([C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:7][C:3]=1[CH:4]=[N:5]O.FC(F)(F)C(OC(=O)C(F)(F)F)=O.C(N(CC)CC)C>O1CCCC1>[OH:1][C:2]1[C:10]([Br:11])=[C:9]([Cl:12])[C:8]([C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:7][C:3]=1[C:4]#[N:5]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 1364045082-Hydroxy-3-bromo-4-chloro-5-(1,1-dimethylethyl)benzaldehyde oxime

Produkt 1

HCID 230354212-Hydroxy-3-bromo-4-chloro-5-(1,1-dimethylethyl)benzonitrileAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

A mixture of 2.20 g (7.18 mmol) of 2-hydroxy-3-bromo-4-chloro-5-(1,1-dimethylethyl)benzaldehyde oxime and 3.12 g (14.72 mmol) of trifluoroacetic anhydride in 15 ml of tetrahydrofuran was cooled in an ice-water bath. A solution of 2.18 g (21.54 mmol) of triethylamine in 10 ml of tetrahydrofuran was added After refluxing for 2 hours, the solvent was evaporated and the residue was partitioned between saturated aqueous sodium bicarbonate solution and ether. The organic phase was washed with 1N hydrochloric acid, followed by water and brine. The organic phase was dried and evaporated. The residue was chromatographed on 100 g of silica gel using a gradient from 5:95 to 50:50 (v/v) ether:hexane as eluent. There was obtained 1.80 g (6.23 mmol, 87%) of 2-hydroxy-3-bromo-4-chloro-5-(1,1-dimethylethyl)benzonitrile; mp 105°-107° C.

Aufarbeitung

  1. temperaturewas cooled in an ice-water bath
  2. temperatureAfter refluxing for 2 hours
  3. customthe solvent was evaporated
  4. customthe residue was partitioned between saturated aqueous sodium bicarbonate solution and ether
  5. washThe organic phase was washed with 1N hydrochloric acid
  6. customThe organic phase was dried
  7. customevaporated
  8. customThe residue was chromatographed on 100 g of silica gel using a gradient from 5:95 to 50:50 (v/v) ether

Quellen und Nachweise

ORD-Eintrag
ord-5190e2e7c062499db417b181bb149ddd
Quelldatensatz
uspto-grants-1990_08
Patentnummer
US04952583

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