Dimethyl Sulfide → 4-Cyano-3-fluorobenzyl bromide

HRID 379036

Reaktionsgleichung

Reaktionsgleichung von HRID 379036
[Br:1]N1C(=O)CCC1=O.CSC.[F:12][C:13]1[CH:20]=[C:19]([CH2:21]O)[CH:18]=[CH:17][C:14]=1[C:15]#[N:16]>C(Cl)Cl>[Br:1][CH2:21][C:19]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[C:13]([F:12])[CH:20]=1

Komponenten

5

Edukt 3

HCID 1068Dimethyl SulfideHCID 67184N-bromobutanimideHCID 118296312-Fluoro-4-(hydroxymethyl)benzonitrile

Produkt 1

HCID 27784664-Cyano-3-fluorobenzyl bromide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

N-Bromosuccinimide (6.6 g, 0.037 mol) was dissolved in CH2Cl2 (150 mL), cooled to 0° C. and treated with dimethylsulfide (3.27 mL, 0.0446 mol). The solution was cooled to −20° C. and then treated dropwise with a solution of 2-fluoro-4-hydroxymethylbenzonitrile (3.74 g, 0.0248 mol) in CH2Cl2 (30 mL). After the addition, the reaction mixture was stirred at 0° C. for 2 h then left to warm to ambient temperature overnight. The reaction mixture was added to ice/H2O, extracted with EtOAc, the organic layer separated, washed with brine and dried (MgSO4). Filtration and concentration to dryness gave the title compound which was purified chromatography (silica gel, 5-10% EtOAc/hexane.

Aufarbeitung

  1. temperatureThe solution was cooled to −20° C.
  2. additionAfter the addition
  3. waitthen left
  4. temperatureto warm to ambient temperature overnight
  5. extractionextracted with EtOAc
  6. customthe organic layer separated
  7. washwashed with brine
  8. dry with materialdried (MgSO4)
  9. filtrationFiltration and concentration to dryness

Quellen und Nachweise

ORD-Eintrag
ord-2fd2548bab09475e9e9d167f92a28e95
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06297239B1

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