(Dimethyl sulfide)trihydroboron → Benzoic acid, 4,5-dichloro-2-(hydroxymethyl)-, methyl ester

HRID 1681944

Reaktionsgleichung

Reaktionsgleichung von HRID 1681944
[C:1]([C:5]1[CH:13]=[C:12]([Cl:14])[C:11]([Cl:15])=[CH:10][C:6]=1[C:7](O)=[O:8])([O:3][CH3:4])=[O:2].B.CSC>C1COCC1>[CH3:4][O:3][C:1](=[O:2])[C:5]1[CH:13]=[C:12]([Cl:14])[C:11]([Cl:15])=[CH:10][C:6]=1[CH2:7][OH:8]

Komponenten

4

Edukt 2

HCID 12423031(Dimethyl sulfide)trihydroboronHCID 198042632-Carbomethoxy 4,5-dichlorobenzoic acid

Produkt 1

HCID 19804259Benzoic acid, 4,5-dichloro-2-(hydroxymethyl)-, methyl esterAusbeute 17 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of the product of Step A (1.06 g, 4.28 mmol) in 5 mL of THF at 0° C. was added borane-methyl sulfide (6.42 mL of 2M solution in THF, 12.84 mmol, 3.0 eq). The reaction was allowed to warm to room temperature. After 16 hours the reaction was cooled to 0° C. and quenched with methanol. The volatiles were removed in vacuo and the oil flash chromatographed with 2:1 hexane/ethyl acetate to yield the titled compound (169 mg, 17%). Approximately 80% of the starting material was also recovered.

Aufarbeitung

  1. temperatureAfter 16 hours the reaction was cooled to 0° C.
  2. customquenched with methanol
  3. customThe volatiles were removed in vacuo
  4. customthe oil flash chromatographed with 2:1 hexane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-e7e5948a6b7e41c4a0abe79c11fc1057
Quelldatensatz
uspto-grants-1992_12
Patentnummer
US05175164

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