Methanol → (5-Fluoro-2-nitrophenyl)methanol

HRID 910104Notes

Reaction equation

HRID 910104 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH:10]=1)[C:7](O)=[O:8].B.CO>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:11]([O-:13])=[O:12])=[C:6]([CH2:7][OH:8])[CH:10]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 6331BoraneHCID 27374205-Fluoro-2-nitrobenzoic acid

Product 1

HCID 12016493(5-Fluoro-2-nitrophenyl)methanolYield 100.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
20 °C

Procedure

Dissolve 5-fluoro-2-nitrobenzoic acid (15 g, 81.08 mmol) in anhydrous tetrahydrofuran (200 mL) and add dropwise with stirring at 20° C. a 1 molar solution of borane in tetrahydrofuran (243 ml, 243 mmol). Stir the mixture at 20° C. for 72 hours then add methanol (200 ml). Concentrate under reduced pressure and purify the residue by flash column chromatography (silica gel, 10-30% ethyl acetate/hexane) to obtain 13.92 g (100%) of the title compound as a white solid.

Workup

  1. additionadd dropwise
  2. concentrationConcentrate under reduced pressure
  3. custompurify the residue by flash column chromatography (silica gel, 10-30% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-18616dde7a2f4632b287c23652a23212
Source dataset
uspto-grants-2011_09
Patent number
US08022065B2

Reaction notes

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