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

HRID 42300

반응식

HRID 42300 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
40 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-394bb218ce9a406696585bd4e93d8732
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536185B2

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