(Dimethyl sulfide)trihydroboron → Methyl 3-bromo-5-(hydroxymethyl)benzoate

HRID 14121

Reaktionsgleichung

Reaktionsgleichung von HRID 14121
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[CH:10]=1)[C:5](O)=[O:6].CSC.B>O1CCCC1>[Br:1][C:2]1[CH:10]=[C:9]([CH:8]=[C:4]([CH2:5][OH:6])[CH:3]=1)[C:11]([O:13][CH3:14])=[O:12]

Komponenten

4

Edukt 2

HCID 12423031(Dimethyl sulfide)trihydroboronHCID 225936413-Bromo-5-(methoxycarbonyl)benzoic acid

Produkt 1

HCID 11356988Methyl 3-bromo-5-(hydroxymethyl)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To an ice-cold, stirred solution of 3-bromo-5-(methoxycarbonyl)benzoic acid (5.0 g, 19.3 mmol) in tetrahydrofuran (77.2 mL) is added borane dimethyl sulfide complex (10.6 mL, 2.0 M tetrahydrofuran, 21.1 mmol). The reaction mixture is heated at 50° C. for 2 h. The reaction mixture is quenched with methanol (50 mL) and concentrated under reduced pressure. Purification by flash column chromatography (silica, 50% ethyl acetate/hexanes) affords the title compound. 1H NMR (300 MHz, CDCl3) δ 8.03 (s, 1H), 7.90 (s, 1H), 7.69 (s, 1H), 4.69 (s, 1H), 3.91 (s, 3H), 2.83 (br s, 1H).

Aufarbeitung

  1. customThe reaction mixture is quenched with methanol (50 mL)
  2. concentrationconcentrated under reduced pressure
  3. customPurification by flash column chromatography (silica, 50% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-6ab5802c15eb4630b4c347d78572be51
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07727997B2

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