Boron tribromide → Ethyl 2-(4-hydroxyphenyl)-4-methyl-1,3-thiazole-5-carboxylate

HRID 250228Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 250228
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([C:11]2[CH:16]=[CH:15][C:14]([O:17]C)=[CH:13][CH:12]=2)=[N:8][C:7]=1[CH3:19])=[O:5])[CH3:2].B(Br)(Br)Br>ClCCl>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([C:11]2[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=2)=[N:8][C:7]=1[CH3:19])=[O:5])[CH3:2]

Komponenten

4

Edukt 2

HCID 25134Boron tribromideHCID 7540952Ethyl 2-(4-methoxyphenyl)-4-methyl-1,3-thiazole-5-carboxylate

Produkt 1

HCID 135509402Ethyl 2-(4-hydroxyphenyl)-4-methyl-1,3-thiazole-5-carboxylateAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a −80° C. solution of 2-(4-methoxy-phenyl)-4-methyl-thiazole-5-carboxylic acid ethyl ester (550 mg, 2 mmol) in dichloromethane (20 mL) is added BBr3 (5 mL, 1M solution in dichloromethane). The reaction is stirred at ambient temperature overnight. The reaction is quenched by addition of methanol and is concentrated in vacuo. The residue is partitioned between EtOAc and 1N HCl. The organic layer is concentrated and the residue is purified by chromatography (0 to 30% EtOAc in hexanes) to give the title compound as a tan solid, (500 mg, 95%). LC-ES/MS m/e 264 (M+1), 1H NMR (DMSO-d6) δ 10.22 (s, 1H), 7.82 (d, 2H), 6.86 (d, 2H), 4.27 (q, 2H), 2.64 (s, 3H), 1.29 (t, 3H).

Aufarbeitung

  1. customThe reaction is quenched by addition of methanol
  2. concentrationis concentrated in vacuo
  3. customThe residue is partitioned between EtOAc and 1N HCl
  4. concentrationThe organic layer is concentrated
  5. customthe residue is purified by chromatography (0 to 30% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-9d782fffaabb4f549ad082d094bccbc4
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863302B2

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