Borane;tetrahydrofuran → 3-Chloro-5-(trifluoromethoxy)benzyl alcohol

HRID 1990724Notes

Reaction equation

HRID 1990724 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([O:11][C:12]([F:15])([F:14])[F:13])[CH:10]=1)[C:5](O)=[O:6].B.C1COCC1>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([O:11][C:12]([F:13])([F:14])[F:15])[CH:10]=1)[CH2:5][OH:6]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 177507353-Chloro-5-(trifluoromethoxy)benzoic acid

Product 1

HCID 177507383-Chloro-5-(trifluoromethoxy)benzyl alcoholYield 100.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-chloro-5-trifluoromethoxybenzoic acid (22.5 g, 93.5 mmol; see step (iv) above) in anhydrous THF (1200 mL) under a N2 atmosphere at room temperature was added a solution of BH3.THF complex (140 mL of 1M in THF; 140.3 mmol). The solution was refluxed for 2 h, cooled to room temperature and stirred for 18 hours, quenched cautiously with H2O and concentrated in vacuo to remove most of the THF. The residue was diluted with EtOAc and the organics were washed with brine (3×), dried (Na2SO4), filtered and concentrated in vacuo to give the crude sub-title compound (21.2 g, 100%) as an oil that was used without further purification.

Workup

  1. temperatureThe solution was refluxed for 2 h
  2. customquenched cautiously with H2O
  3. concentrationconcentrated in vacuo
  4. customto remove most of the THF
  5. additionThe residue was diluted with EtOAc
  6. washthe organics were washed with brine (3×)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4fa6c080e09544f18dacc2a7104775f0
Source dataset
uspto-grants-2010_01
Patent number
US07645751B2

Reaction notes

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