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

HRID 252466Notes

Reaction equation

HRID 252466 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]([N+:12]([O-:14])=[O:13])=[CH:9][C:10]=1[F:11])[C:5](O)=[O:6].CO>C1COCC1>[F:11][C:10]1[C:2]([F:1])=[CH:3][C:4]([CH2:5][OH:6])=[C:8]([N+:12]([O-:14])=[O:13])[CH:9]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 42196304,5-Difluoro-2-nitrobenzoic acid

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3,4-difluoro-6-nitrobenzoic acid (3.05 g, 15 mmol) in THF (20 mL) was added BH3 THF (30 mL). The resulting mixture was stirred at room temperature for 2 h and then at 50° C. for 5 h. The resulting mixture was then cooled to room temperature, and methanol (20 mL) was added slowly. The resulting mixture was concentrated, and the residue was treated with methanol twice more, to yield a yellow solid.

Workup

  1. waitat 50° C. for 5 h
  2. temperatureThe resulting mixture was then cooled to room temperature
  3. concentrationThe resulting mixture was concentrated
  4. additionthe residue was treated with methanol twice more
  5. customto yield a yellow solid

Sources & evidence

ORD record
ord-6848fa55f13349e3a09172e81b693666
Source dataset
uspto-grants-2011_01
Patent number
US07868022B2

Reaction notes

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