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

HRID 541792

반응식

HRID 541792 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 279258(2-Iodo-4-nitrophenyl)methanol수율 67%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-2e76ffa7ba754aa7b26495467834c37d
출처 데이터셋
uspto-grants-2014_10
특허 번호
US08871753B2

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