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

HRID 2107589Notes

Reaction equation

HRID 2107589 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-575e321182794db08d2729f29ca5004e
Source dataset
uspto-grants-1990_06
Patent number
US04935420

Reaction notes

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