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

HRID 250228노트

반응식

HRID 250228 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-9d782fffaabb4f549ad082d094bccbc4
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863302B2

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