O-Cresol → 4-Iodo-2-methylphenol

HRID 263495노트

반응식

HRID 263495 반응식
[C:1]1([CH3:8])[C:6]([OH:7])=[CH:5][CH:4]=[CH:3][CH:2]=1.[Na+].[I-:10].CC1C=CC(S([N-]Cl)(=O)=O)=CC=1.O.[Na+].O>CN(C=O)C>[I:10][C:3]1[CH:4]=[CH:5][C:6]([OH:7])=[C:1]([CH3:8])[CH:2]=1

참가 물질

6

반응물 4

HCID 335O-CresolHCID 962WaterHCID 5238Sodium IodideHCID 16218604312693-78-0

생성물 1

HCID 1437134-Iodo-2-methylphenol수율 63%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 10 g of o-cresol and 16.5 g (1.2 equiv) NaI in 250 ml of DMF was added 31 g (1.2 equiv) of chloramine-T hydrate. The dark green solution was stirred at rt for 1.5 h. The mixture, now a heterogeneous light brown, was poured into water, acidified, extracted with ethyl acetate, and the organic phase washed with water and bisulfite solution. The organic phase was dried over MgSO4. Concentration, trituration with hexane, and flash chromatography (silica gel, hexane, hexane/ethyl acetate (5:1)) provided 13.6 g (63%) of the title compound as a white solid.

후처리

  1. extractionextracted with ethyl acetate
  2. washthe organic phase washed with water and bisulfite solution
  3. dry with materialThe organic phase was dried over MgSO4
  4. concentrationConcentration, trituration with hexane, and flash chromatography (silica gel, hexane, hexane/ethyl acetate (5:1))

출처 및 근거

ORD 기록
ord-ce2ea1557f0747248102c3fba64c305e
출처 데이터셋
uspto-grants-1997_07
특허 번호
US05643929

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