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

HRID 541792

Reaction equation

HRID 541792 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-2e76ffa7ba754aa7b26495467834c37d
Source dataset
uspto-grants-2014_10
Patent number
US08871753B2

Linked notes

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