Water → (2-Iodo-4-nitrophenyl)methanol

HRID 541792

反応式

HRID 541792 の反応式
[I:1][C:2]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:3]=1[C:4](OC)=[O:5].[BH4-].[Li+].O.C(OCC)(=O)C>C1COCC1>[I:1][C:2]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:3]=1[CH2:4][OH:5]

参加物

6

反応物 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 232745Methyl 2-iodo-4-nitrobenzoateHCID 4148881Lithium borohydride

生成物 1

HCID 279258(2-Iodo-4-nitrophenyl)methanol収率 67%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of methyl 2-iodo-4-nitrobenzoate (25.6 g, 83.4 mmol) in THF (400 mL) was added lithium tetrahydroborate (2.2 g, 92 mmol). The reaction solution was stirred at rt for 2 h and cooled down to 0° C., and water was added dropwise. After stirring for 10 min, ethyl acetate was added. The organic solution was separated and washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified with flash chromatography (30% ethyl acetate/hexs) to give the desired product as yellow solid (15.6 g, 67%). LCMS calculated for C7H71NO3(M+H)+: m/z=280.0.

後処理

  1. temperaturecooled down to 0° C.
  2. stirringAfter stirring for 10 min
  3. customThe organic solution was separated
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified with flash chromatography (30% ethyl acetate/hexs)

出典と根拠

ORDレコード
ord-2e76ffa7ba754aa7b26495467834c37d
出典データセット
uspto-grants-2014_10
特許番号
US08871753B2

関連ノート

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