4-(Bromomethyl)benzoic acid → 4-(Bromomethyl)benzyl alcohol

HRID 5926

Reaktionsgleichung

Reaktionsgleichung von HRID 5926
[Br:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7](O)=[O:8])=[CH:5][CH:4]=1.B.C1COCC1>C1COCC1>[Br:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([CH2:7][OH:8])=[CH:5][CH:4]=1

Komponenten

4

Edukt 2

HCID 225994-(Bromomethyl)benzoic acidHCID 2723981Borane;tetrahydrofuran

Produkt 1

HCID 103304344-(Bromomethyl)benzyl alcoholAusbeute 94,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A suspension of 4-bromomethylbenzoic acid (5.04; 23.3 mmol) in THF (30 ml) was cooled to 0° C. and treated with borane/THF (35 mmol). The ice bath was removed and the mixture was allowed to warm to room temperature and stirred for 1.5 hours. The excess borane was quenched with MeOH, and then with water, and the reaction mixture was concentrated in vacuo. The residue was dissolved in ethyl acetate and washed with 4% HCl, water NaHCO3, brine, dried (MgSO4), filtered, concentrated in vacuo to afford 4.44 g (94%) of the title compound.

Aufarbeitung

  1. customThe ice bath was removed
  2. temperatureto warm to room temperature
  3. customThe excess borane was quenched with MeOH
  4. concentrationwith water, and the reaction mixture was concentrated in vacuo
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. washwashed with 4% HCl, water NaHCO3, brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-64a0c4283173496db827ea2c2506a2c6
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05246944

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