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

HRID 250228

反応式

HRID 250228 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-9d782fffaabb4f549ad082d094bccbc4
出典データセット
uspto-grants-2011_01
特許番号
US07863302B2

関連ノート

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