4-Bromo-2,5-difluoronitrobenzene → 5-Bromo-4-fluoro-2-nitrophenol

HRID 661076

반응식

HRID 661076 반응식
C[Si](C)(C)[O-:3].[Na+].[Br:7][C:8]1[C:13]([F:14])=[CH:12][C:11]([N+:15]([O-:17])=[O:16])=[C:10](F)[CH:9]=1>C1COCC1>[Br:7][C:8]1[C:13]([F:14])=[CH:12][C:11]([N+:15]([O-:17])=[O:16])=[C:10]([OH:3])[CH:9]=1

참가 물질

4

반응물 2

HCID 27362864-Bromo-2,5-difluoronitrobenzeneHCID 23672319Sodium trimethylsilanolate

생성물 1

HCID 576341145-Bromo-4-fluoro-2-nitrophenol수율 205.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 2 M sodium trimethylsilanolate (15.6, 31.1 mmol) in THF was added dropwise to 4-bromo-2,5-difluoronitrobenzene (2.47 g, 10.4 mmol) under a nitrogen atmosphere. A bright red suspension was formed, and the mixture was refluxed for 27 hours. The mixture was cooled to room temperature and concentrated. Water (6 mL) was added, and the solution was acidified with a 10% HCl solution, extracted with DCM (70 mL×2). The organic layers were combined and concentrated to give 5-bromo-4-fluoro-2-nitrophenol (5.05 g, 2.06%). MS m/z: 236 (M+1). 1H NMR (400 MHz, CD3OD) δ ppm 7.48 (d, J=5.87 Hz, 1H), 7.95 (d, J=8.41 Hz, 1H).

후처리

  1. customA bright red suspension was formed
  2. temperaturethe mixture was refluxed for 27 hours
  3. concentrationconcentrated
  4. additionWater (6 mL) was added
  5. extractionextracted with DCM (70 mL×2)
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-ed676f995b4443068691f4bacd65cbcc
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084479B2

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