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

HRID 243218ノート

反応式

HRID 243218 の反応式
[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]

参加物

5

反応物 1

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

生成物 1

HCID 537967812,6-Difluoro-3-nitrophenol

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 260Hydrogen Bromide溶媒HCID 1140Toluene溶媒

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-01b08e7178e64423bbd50f21c446c827
出典データセット
uspto-grants-2014_02
特許番号
US08653089B2

反応ノート

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