Iodine → 4-hydroxy-3-methoxy-2-nitrobenzonitrile

HRID 536228노트

반응식

HRID 536228 반응식
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[C:4]([N+:10]([O-:12])=[O:11])[C:3]=1[O:13][CH3:14].[OH-].[NH4+:16].II>C1COCC1>[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:16])=[C:4]([N+:10]([O-:12])=[O:11])[C:3]=1[O:13][CH3:14]

참가 물질

5

반응물 3

HCID 807IodineHCID 14923Ammonium HydroxideHCID 96959Benzaldehyde, 4-hydroxy-3-methoxy-2-nitro-

생성물 1

HCID 70592654-hydroxy-3-methoxy-2-nitrobenzonitrile수율 84%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

4-Hydroxy-3-methoxy-2-nitrobenzaldehyde (200 g, 1.01 mol) was dissolved in THF (2.5 L) and then ammonium hydroxide (2.5 L) was added followed by iodine (464 g, 1.8 mol). The resulting mixture was allowed to stir for 2 days at which time it was concentrated under reduced pressure. The residue was acidified with HCl (2 N) and extracted into diethyl ether. The organic layer was washed with brine and dried (sodium sulfate) and concentrated under reduced pressure. The residue was washed with diethyl ether and dried under vacuum to provide the title compound (166 g, 84%): 1H NMR (DMSO-d6) δ: 11.91 (1H, s), 7.67 (1H, d), 7.20 (1H, d), 3.88 (3H, s)

후처리

  1. concentrationwas concentrated under reduced pressure
  2. extractionextracted into diethyl ether
  3. washThe organic layer was washed with brine
  4. dry with materialdried (sodium sulfate)
  5. concentrationconcentrated under reduced pressure
  6. washThe residue was washed with diethyl ether
  7. customdried under vacuum

출처 및 근거

ORD 기록
ord-041f6e276e7049b592989eb8f16fc7b0
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08859572B2

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