2-Bromo-2'-hydroxyacetophenone → 2-[2-(Trifluoromethyl)-1,3-thiazol-4-yl]phenol

HRID 2178650

反応式

HRID 2178650 の反応式
[F:1][C:2]([F:7])([F:6])[C:3](=[S:5])[NH2:4].[P].[S].Br[CH2:11][C:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[OH:20])=O>C(O)C>[F:1][C:2]([F:7])([F:6])[C:3]1[S:5][CH:11]=[C:12]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[OH:20])[N:4]=1

参加物

6

反応物 4

HCID 2006712-Bromo-2'-hydroxyacetophenoneHCID 4425751TrifluoroethanethioamideHCID 5362487SulfurHCID 5462309Phosphorus

生成物 1

HCID 683799052-[2-(Trifluoromethyl)-1,3-thiazol-4-yl]phenol

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

実験手順

2,2,2-Trifluoroethanethioamide (which may be prepared by the method of J. H. Hillhouse et al., Phosphorus, Sulfur Relat. Elem. 1986, 26, 169-84) (157 mg, 1.22 mmol) in ethanol (1.3 mL) was added drop-wise to a solution of 2-bromo-1-(2-hydroxyphenyl)ethanone (119 mg, 0.55 mmol) in ethanol (1.3 mL) and the reaction was refluxed overnight. The reaction was concentrated in vacuo and purified via silica gel chromatography (Gradient: 5% to 20% ethyl acetate in heptane) to afford the title compound. Yield: 67 mg, 0.27 mmol, 49%. LCMS m/z 246.0 (M+1). 1H NMR (400 MHz, CDCl3) δ 6.95 (ddd, J=8, 7, 1 Hz, 1H), 7.07 (dd, J=8.2, 1.2 Hz, 1H), 7.33 (ddd, J=8, 7, 2 Hz, 1H), 7.64 (dd, J=7.8, 1.6 Hz, 1H), 7.81 (s, 1H), 10.47 (s, 1H).

後処理

  1. temperaturethe reaction was refluxed overnight
  2. concentrationThe reaction was concentrated in vacuo
  3. custompurified via silica gel chromatography (Gradient: 5% to 20% ethyl acetate in heptane)

出典と根拠

ORDレコード
ord-7a31637b6a114285a763360b902a4d7c
出典データセット
uspto-grants-2015_06
特許番号
US09067934B2

関連ノート

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