Dimethylformamide → 3-(Benzyloxy)-4-bromophenol

HRID 26084

Reaktionsgleichung

Reaktionsgleichung von HRID 26084
[H-].[K+].CN(C)C=O.[Br:8][C:9]1[CH:15]=[CH:14][C:12]([OH:13])=[CH:11][C:10]=1[OH:16].[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>CCOCC.O>[CH2:17]([O:16][C:10]1[CH:11]=[C:12]([OH:13])[CH:14]=[CH:15][C:9]=1[Br:8])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 811054-BromoresorcinolHCID 82127Potassium hydride

Produkt 1

HCID 156706543-(Benzyloxy)-4-bromophenol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a 0° C. slurry of 1.7 g. (42.5 mmoles) of potassium hydride in 35 ml. of N,N-dimethylformamide is slowly added a solution of 7.22 g. (38.2 mmoles) of 4-bromoresorcinol. The resultant mixture is stirred for 30 minutes and then 4.54 ml. (38.2 mmoles) of benzyl bromide is slowly added. The reaction mixture is stirred 3 hours longer at 0° C. and then added to 200 ml. of cold water and 200 ml. of ether. The ether extract is washed twice with 200 ml. portions of water, dried over magnesium sulfate and evaporated to an oil. The crude oil is purified via column chromatography on 400 g. of silica gel eluted with 25% ether-pentane to yield (in order of elution) 2.2 g. (16%) of 2,4-dibenzyloxybromobenzene, 0.21 g. (2%) of 5-benzyloxy-2-bromophenol and 3.52 g. (33%) of 3-benzyloxy-4-bromophenol.

Aufarbeitung

  1. customTo a 0° C.
  2. additionadded to 200 ml
  3. extractionThe ether extract
  4. washis washed twice with 200 ml
  5. dry with materialportions of water, dried over magnesium sulfate
  6. customevaporated to an oil
  7. customThe crude oil is purified via column chromatography on 400 g
  8. washof silica gel eluted with 25% ether-pentane
  9. customto yield
  10. wash(in order of elution) 2.2 g

Quellen und Nachweise

ORD-Eintrag
ord-cbaf3fd342894c14a78febb86ca2b7a8
Quelldatensatz
uspto-grants-1979_04
Patentnummer
US04147872

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