Tetrahydrofuran → (4,5-Difluoro-2-nitrophenyl)methanol

HRID 658065Notes

Reaction equation

HRID 658065 reaction equation
[F:1][C:2]1[C:10]([F:11])=[CH:9][C:5]([C:6](O)=[O:7])=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=1.C1COCC1>CO>[F:1][C:2]1[C:10]([F:11])=[CH:9][C:5]([CH2:6][OH:7])=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=1

Participants

4

Reactant 2

HCID 8028Tetrahydrofuran2×HCID 42196304,5-Difluoro-2-nitrobenzoic acid

Product 1

HCID 57475722(4,5-Difluoro-2-nitrophenyl)methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

4,5-Difluoro-2-nitro-benzoic acid (3.05 g, 15 mmol) was combined with THF (20 mL), and then BH3 THF (35 mL) was added over 15 min. The resulting mixture was stirred overnight at 60° C. and then cooled to room temperature. Methanol was added, and the resulting mixture was stirred 15 min. The solvent was removed to yield an oil, which was purified by silica gel chromatography to yield a residue.

Workup

  1. temperaturecooled to room temperature
  2. stirringthe resulting mixture was stirred 15 min
  3. customThe solvent was removed
  4. customto yield an oil, which
  5. customwas purified by silica gel chromatography
  6. customto yield a residue

Sources & evidence

ORD record
ord-88247b6c27f640beb04eed42e43c2149
Source dataset
uspto-grants-2011_12
Patent number
US08076358B2

Reaction notes

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