Hydrochloric Acid → 3-Fluoro-4-nitrobenzyl alcohol

HRID 2261089Notes

Reaction equation

HRID 2261089 reaction equation
[BH4-].[Na+].[F:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])[C:7](O)=[O:8].B(F)(F)F.CCOCC.Cl>C1COCC1>[F:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[N+:13]([O-:15])=[O:14])[CH2:7][OH:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8000Boron trifluoride etherateHCID 2306533-Fluoro-4-nitrobenzoic acidHCID 4311764Sodium borohydride

Product 1

HCID 27746583-Fluoro-4-nitrobenzyl alcoholYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To an ice-cooled suspension of NaBH4 (204 mg, 5.4 mmol, 2 eq.) in THF (10 mL) was added dropwise 3-fluoro 4-nitro benzoic acid (500 mg, 2.7 mmol, 1 eq.) in THF (10 mL) over 30 minutes. BF3-Et2O (7.3 mmol, 2.7 eq.) was then added dropwise over 30 minutes. The solution was stirred at room temperature over night. 1N HCl was added dropwise to quench NaBH4 excess. The solvent was removed in vacuo, the residue dissolved in DCM, washed with water, brine. The organic layer was then dried over MgSO4 and the solvent removed in vacuo to give 425 mg of 3-fluoro 4-nitro benzyl alcohol (92% yield). The compound was used in the following step with no further purification.

Workup

  1. customto quench NaBH4 excess
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue dissolved in DCM
  4. washwashed with water, brine
  5. dry with materialThe organic layer was then dried over MgSO4
  6. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-93fb2d3ab55d46db816af3374ac390cf
Source dataset
uspto-grants-2010_12
Patent number
US07846925B2

Reaction notes

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