O-Cresol → 4-Iodo-2-methylphenol

HRID 263495ノート

反応式

HRID 263495 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 1437134-Iodo-2-methylphenol収率 63%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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))

出典と根拠

ORDレコード
ord-ce2ea1557f0747248102c3fba64c305e
出典データセット
uspto-grants-1997_07
特許番号
US05643929

反応ノート

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