Methanol → (2,3-Difluoro-5-nitrophenyl)methanol

HRID 2277752Notes

Reaction equation

HRID 2277752 reaction equation
[F:1][C:2]1[C:10]([F:11])=[CH:9][C:8]([N+:12]([O-:14])=[O:13])=[CH:7][C:3]=1[C:4](O)=[O:5].CO>C1COCC1.C(OCC)(=O)C>[F:1][C:2]1[C:10]([F:11])=[CH:9][C:8]([N+:12]([O-:14])=[O:13])=[CH:7][C:3]=1[CH2:4][OH:5]

Participants

5

Reactant 2

HCID 887MethanolHCID 545937902,3-Difluoro-5-nitrobenzoic acid

Product 1

HCID 68806779(2,3-Difluoro-5-nitrophenyl)methanol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a stirring solution of 2,3-difluoro-5-nitrobenzoic acid (Butt Park Ltd.; 9.00 g; 44.3 mmol) in THF at 0° C. was added a 1M solution of borane-tetrahydrofuran complex in THF (177.3 mL; 177.3 mmol). The mixture was allowed to react at RT overnight. Then, MeOH was cautiously added to the stirred mixture while cooling with an ice bath. The batch was diluted with ethyl acetate and washed with aqueous sodium hydroxide solution (1N) and saturated aqueous sodium chloride solution. The organic phase was dried (sodium sulfate), filtered and concentrated. The residue was purified by chromatography (hexane to hexane/ethyl acetate 1:2) to give the pure product (8.20 g; 43.4 mmol).

Workup

  1. customto react at RT overnight
  2. temperaturewhile cooling with an ice bath
  3. washwashed with aqueous sodium hydroxide solution (1N) and saturated aqueous sodium chloride solution
  4. dry with materialThe organic phase was dried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography (hexane to hexane/ethyl acetate 1:2)
  8. customto give the pure product (8.20 g; 43.4 mmol)

Sources & evidence

ORD record
ord-d0443bcf5a4149899511b21693106d11
Source dataset
uspto-grants-2015_09
Patent number
US09133171B2

Reaction notes

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