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

HRID 2351899Notes

Reaction equation

HRID 2351899 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-3a612d3f4a8e44acab6660fe9e35d944
Source dataset
uspto-grants-1989_10
Patent number
US04874764

Reaction notes

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