Boron trifluoride etherate → 2,3,6-Trifluoro-5-nitrobenzenemethanol

HRID 1722283Notes

Reaction equation

HRID 1722283 reaction equation
[OH-].[B+3].[Na+].[OH-].[OH-].[OH-].[F:7][C:8]1[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][C:14]([F:20])=[C:13]([F:21])[C:9]=1[C:10](O)=[O:11].B(F)(F)F.CCOCC>O1CCCC1>[F:7][C:8]1[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][C:14]([F:20])=[C:13]([F:21])[C:9]=1[CH2:10][OH:11]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 156318282,3,6-Trifluoro-5-nitrobenzoic acidHCID 178419133HCID 178419133, compound

Product 1

HCID 156318292,3,6-Trifluoro-5-nitrobenzenemethanolYield 67.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of sodium boron hydroxide (44 g) in anhydrous tetrahydrofuran is added a solution of 2,5,6-trifluoro-3-nitrobenzoic acid (22 g) in anhydrous tetrahydrofuran (40 ml) at below 10° C., and thereto is further added dropwise a solution of boron trifluoride etherate (20 ml) in anhydrous tetrahydrofuran (40 ml) at below 10° C. After the addition, the mixture is stirred at room temperature for one hour. The reaction mixture is poured into ice water and extracted with diethyl ether. The extract is dried, and then the solvent is distilled off to give 2,5,6-trifluoro-3-nitrobenzyl alcohol (14 g).

Workup

  1. additionAfter the addition
  2. extractionextracted with diethyl ether
  3. customThe extract is dried
  4. distillationthe solvent is distilled off

Sources & evidence

ORD record
ord-04be2b09ba804c04ad0f8f63e2d1bb9e
Source dataset
uspto-grants-1989_08
Patent number
US04855292

Reaction notes

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