2-Fluoro-5-nitrobenzoic acid → (2-Fluoro-5-nitrophenyl)methanol

HRID 1796627Notes

Reaction equation

HRID 1796627 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4](O)=[O:5].B.C1COCC1>C1COCC1>[F:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[CH2:4][OH:5]

Participants

4

Reactant 2

HCID 2809972-Fluoro-5-nitrobenzoic acidHCID 2723981Borane;tetrahydrofuran

Product 1

HCID 4437169(2-Fluoro-5-nitrophenyl)methanolYield 100.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-fluoro-5-nitro-benzoic acid (2.9 g, 15.7 mmol) in THF (20 ml) was slowly added 1M BH3.THF (30 ml, 30 mmol) at 0° C. The reaction mixture was stirred at rt overnight, quenched carefully with MeOH until no H2 evolution, evaporated and redissolved in MeOH, evaporated again to give 394A (2.7 g, 100%) as a yellow solid.

Workup

  1. customat 0° C
  2. customquenched carefully with MeOH until no H2 evolution
  3. customevaporated
  4. dissolutionredissolved in MeOH
  5. customevaporated again

Sources & evidence

ORD record
ord-c205dd16a18549eb9551af0774e2e606
Source dataset
uspto-grants-2006_04
Patent number
US07030112B2

Reaction notes

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