Hexane → 2-Bromo-1-(2-phenoxypyrimidin-5-yl)ethanone

HRID 42300

反応式

HRID 42300 の反応式
[O:1]([C:8]1[N:13]=[CH:12][C:11]([C:14](=[O:16])[CH3:15])=[CH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br-:17].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.CCCCCC>ClCCl>[Br:17][CH2:15][C:14]([C:11]1[CH:12]=[N:13][C:8]([O:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[N:9][CH:10]=1)=[O:16]

参加物

5

反応物 3

HCID 8058HexaneHCID 23500184Tetra-n-butylammonium tribromideHCID 592524401-(2-Phenoxypyrimidin-5-yl)ethanone

生成物 1

HCID 592524262-Bromo-1-(2-phenoxypyrimidin-5-yl)ethanone収率 68.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
40 °C

実験手順

To a solution consisting of 1-(2-phenoxypyrimidin-5-yl)ethanone (Step B, 400 mg, 1.87 mmol) in dichloromethane (14 mL) was added tetrabutylammonium tribromide (990 mg, 2.05 mmol). The reaction mixture was sealed with a screw top and warmed at 40° C. overnight and allowed to cool to room temperature. Hexane (4 mL) was subsequently added. After three hours and little precipitation, additional (150 mg) tetrabutylammonium tribromide was added and the reaction mixture was stirred overnight at room temperature. The pale yellow precipitate that formed was collected on a filter and washed with 1:1 dichloromethane-hexane to afford the title intermediate (375 mg, 68%); Rf 0.43 with 3:1 v/v hexanes-ethyl acetate; MS (ESI+) m/z 295, 293 (M+1, Br isotopes).

後処理

  1. customThe reaction mixture was sealed with a screw top
  2. temperatureto cool to room temperature
  3. customlittle precipitation, additional (150 mg) tetrabutylammonium tribromide
  4. additionwas added
  5. customThe pale yellow precipitate that formed
  6. customwas collected on
  7. filtrationa filter
  8. washwashed with 1:1 dichloromethane-hexane

出典と根拠

ORDレコード
ord-394bb218ce9a406696585bd4e93d8732
出典データセット
uspto-grants-2013_09
特許番号
US08536185B2

関連ノート

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