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Boron tribromide → 4-[5-(2-Fluorophenoxy)oxazolo[5,4-d]pyrimidin-2-yl]-2,6-dimethylphenol

HRID 576912
ノート
印刷プレビュー

反応式

HRID 576912 の反応式
[F:1][C:2]1[CH:27]=[CH:26][CH:25]=[CH:24][C:3]=1[O:4][C:5]1[N:6]=[CH:7][C:8]2[N:13]=[C:12]([C:14]3[CH:19]=[C:18]([CH3:20])[C:17]([O:21]C)=[C:16]([CH3:23])[CH:15]=3)[O:11][C:9]=2[N:10]=1.B(Br)(Br)Br.C(=O)([O-])O.[Na+]>ClCCl>[F:1][C:2]1[CH:27]=[CH:26][CH:25]=[CH:24][C:3]=1[O:4][C:5]1[N:6]=[CH:7][C:8]2[N:13]=[C:12]([C:14]3[CH:15]=[C:16]([CH3:23])[C:17]([OH:21])=[C:18]([CH3:20])[CH:19]=3)[O:11][C:9]=2[N:10]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 25134Boron tribromide2 回HCID 516892Sodium BicarbonateHCID 533113735-(2-Fluoro-phenoxy)-2-(4-methoxy-3,5-dimethyl-phenyl)-oxazolo[5,4-d]pyrimidine

生成物 1

HCID 1361211154-[5-(2-Fluorophenoxy)oxazolo[5,4-d]pyrimidin-2-yl]-2,6-dimethylphenol収率 90.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒3 回

反応条件

温度
0 °C

実験手順

A solution of 510 mg of 5-(2-fluoro-phenoxy)-2-(4-methoxy-3,5-dimethyl-phenyl)-oxazolo[5,4-d]pyrimidine in 20 ml of dichloromethane was cooled to 0° C. Over a period of 10 min, 4.2 ml of a 1 M solution of boron tribromide in dichloromethane was added. The mixture was stirred at 0° C. for 1 h, and then another 2 ml of a 1 M solution of boron tribromide in dichloromethane were added. After stirring for another 1 h, 10 ml of a saturated aqueous solution of sodium hydrogencarbonate were added slowly. The aqueous layer was extracted twice with 15 ml of dichloromethane, and the combined organic layers were dried over sodium sulfate, filtered. The solvents were removed in vacuo to give 445 mg of the title compound as a white solid. LC/MS (method LC2): Rt=3.62 min; m/z=352.13 [M+H]+

後処理

  1. stirringAfter stirring for another 1 h
  2. extractionThe aqueous layer was extracted twice with 15 ml of dichloromethane
  3. dry with materialthe combined organic layers were dried over sodium sulfate
  4. filtrationfiltered
  5. customThe solvents were removed in vacuo

出典と根拠

ORDレコード
ord-fbcc6ef97e944388a553ebab3aaff62d
出典データセット
uspto-grants-2015_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09040544B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート