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

HRID 910765Notes

Reaction equation

HRID 910765 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.B.O1CCCC1.CO>C1COCC1>[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

5

Reactant 3

HCID 887MethanolHCID 2723981Borane;tetrahydrofuranHCID 42196304,5-Difluoro-2-nitrobenzoic acid

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of to 4,5-difluoro-2-nitrobenzoic acid (25.9 g) in THF (90 ml), cooled to 0° C., was carefully added borane-tetrahydrofuran complex (319 ml, 1M in THF). After the addition was complete, the mixture was stirred at 60° C. for 3 h. Methanol (150 ml) was added to the mixture at 0° C. and after 10 minutes the mixture was concentrated in vacuo. The residue was poured into water and extracted with ethyl acetate. The organic layer was washed with sat. aq. NaCl, dried (MgSO4), filtered and concentrated in vacuo.

Workup

  1. additionAfter the addition
  2. concentrationwas concentrated in vacuo
  3. additionThe residue was poured into water
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with sat. aq. NaCl
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3154be931743426e9e0a4e705f9b1e44
Source dataset
uspto-grants-2011_09
Patent number
US08022218B2

Reaction notes

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