Benzyl Alcohol → 1-(Benzyloxy)-3-fluoro-2-nitrobenzene

HRID 730558노트

반응식

HRID 730558 반응식
[H-].[Na+].[CH2:3]([OH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[F:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14](F)[C:13]=1[N+:19]([O-:21])=[O:20].O>CN(C=O)C.C(OCC)(=O)C>[CH2:3]([O:10][C:14]1[CH:15]=[CH:16][CH:17]=[C:12]([F:11])[C:13]=1[N+:19]([O-:21])=[O:20])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

참가 물질

7

반응물 4

HCID 244Benzyl AlcoholHCID 962WaterHCID 24758Sodium hydrideHCID 879221,3-Difluoro-2-nitrobenzene

생성물 1

HCID 578349821-(Benzyloxy)-3-fluoro-2-nitrobenzene수율 87%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a suspension of sodium hydride (1.522 g, 38.06 mmol) in anhydrous DMF (150 mL) at room temperature was added benzyl alcohol (3.44 mL, 33.3 mmol) dropwise over 10 minutes, and stirring was continued for another 10 minutes. 2,6-Difluoronitrobenzene (5.046 g, 31.72 mmol) was added to the reaction mixture in one portion. The reaction mixture was stirred for an hour, and 100 mL water and 100 mL ethyl acetate were added. The layers were separated, and the aqueous layer was extracted with 75 mL ethyl acetate. The combined organic layers were washed with 100 mL water and 100 mL brine, dried over sodium sulfate and concentrated in vacuo. The resulting residue was purified by flash chromatography (6% to 35% ethyl acetate in hexanes) to give 6.818 g (27.6 mmol, 87%) of 1-benzyloxy-3-fluoro-2-nitro-benzene as a yellow oil. MS: 248 (M+H)+.

후처리

  1. stirringThe reaction mixture was stirred for an hour
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with 75 mL ethyl acetate
  4. washThe combined organic layers were washed with 100 mL water and 100 mL brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified by flash chromatography (6% to 35% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-7b700593b83e420c8472593301e35ca4
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07582760B2

반응 노트

불러오는 중…