Boron trifluoride → 2-(2-Chloro-6-nitrophenyl)ethanol

HRID 1656746

Reaction equation

HRID 1656746 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-:12])=[O:11])[C:5]=1[CH2:13][C:14](O)=[O:15].B(F)(F)F.C(=O)([O-])O.[Na+]>C(Cl)Cl.O.O1CCCC1>[Cl:3][C:4]1[C:5]([CH2:13][CH2:14][OH:15])=[C:6]([N+:10]([O-:12])=[O:11])[CH:7]=[CH:8][CH:9]=1

Participants

8

Reactant 4

HCID 6356Boron trifluorideHCID 271550(2-Chloro-6-nitrophenyl)acetic acidHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydride

Product 1

HCID 7008102-(2-Chloro-6-nitrophenyl)ethanolYield 86%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

2.26 g (59.8 mmol) of sodium borohydride was added to 7 ml of tetrahydrofuran, and while cooling on ice, 15 ml of tetrahydrofuran solution containing 6.78 g (31.5 mmol) of the compound (137) obtained above was dropped to the solution through 20 minutes. Then, 15 ml of tetrahydrofuran solution containing 10 ml of borontrifluoride--ether complex was dropped to the solution through 10 minutes, and after stirring for 30 minutes as was, the solution was stirred for 1 hour at room temperature. To 130 ml of water containing 9.6 g of sodium hydrogen carbonate and 170 ml of methylene chloride, the reaction solution was added slowly, and the obtained solution was stirred overnight at room temperature. The organic layer was separated, and after drying over magnesium sulfate, the solvent was removed by distillation. To the residue, n-hexane was added to crystallize, and the crystals were filtered off and washed with n-hexane to obtain 5.43 g of the subject compound (138) in a 86% yield.

Workup

  1. customobtained
  2. additionabove was dropped to the solution through 20 minutes
  3. additionether complex was dropped to the solution through 10 minutes
  4. stirringthe solution was stirred for 1 hour at room temperature
  5. stirringthe obtained solution was stirred overnight at room temperature
  6. customThe organic layer was separated
  7. dry with materialafter drying over magnesium sulfate
  8. customthe solvent was removed by distillation
  9. additionTo the residue, n-hexane was added
  10. customto crystallize
  11. filtrationthe crystals were filtered off
  12. washwashed with n-hexane

Sources & evidence

ORD record
ord-38ccc6a08aa0476cb70e355556845aa4
Source dataset
uspto-grants-1993_10
Patent number
US05254685

Linked notes

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