1,3-Difluoro-2-methoxy-4-nitrobenzene → 2,6-Difluoro-3-nitrophenol

HRID 243218노트

반응식

HRID 243218 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([F:11])[C:3]=1[O:12]C>Br.CC(O)=O.C1(C)C=CC=CC=1>[F:11][C:4]1[C:5]([N+:8]([O-:10])=[O:9])=[CH:6][CH:7]=[C:2]([F:1])[C:3]=1[OH:12]

참가 물질

5

반응물 1

HCID 681577701,3-Difluoro-2-methoxy-4-nitrobenzene

생성물 1

HCID 537967812,6-Difluoro-3-nitrophenol

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 260Hydrogen Bromide용매HCID 1140Toluene용매

실험 절차

A solution of 1,3-difluoro-2-methoxy-4-nitrobenzene (0.50 g, 2.644 mmol) in 33% HBr in AcOH (4 mL) was heated at 100° C. for 1 h using microwave irradiation. The cooled reaction mixture was diluted with toluene and concentrated in vacuo. The resulting residue was partitioned between aqueous NaHCO3 and EtOAc. The aqueous phase was acidified with 1M HCl and extracted twice with DCM. The combined DCM extracts were washed with water, dried (Na2SO4) and concentrated in vacuo affording the title compound as a buff solid (0.29 g, 63%). 1H NMR (CDCl3, 300 MHz): 7.70 (1H, ddd, J=9.5, 7.8, 5.4 Hz), 7.06 (1H, ddd, J=9.4, 9.0, 2.2 Hz), 5.61 (1H, bs)

후처리

  1. custommicrowave irradiation
  2. customThe cooled reaction mixture
  3. concentrationconcentrated in vacuo
  4. customThe resulting residue was partitioned between aqueous NaHCO3 and EtOAc
  5. extractionextracted twice with DCM
  6. washThe combined DCM extracts were washed with water
  7. dry with materialdried (Na2SO4)
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-01b08e7178e64423bbd50f21c446c827
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653089B2

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