Sodium borohydride → 1-(4-{[4-Chloro-3-(trifluoromethyl)phenyl]oxy}phenyl)ethanol

HRID 705856Notes

Reaction equation

HRID 705856 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15](=[O:17])[CH3:16])=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:18]([F:21])([F:20])[F:19].[BH4-].[Na+]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:10]=[CH:11][C:12]([CH:15]([OH:17])[CH3:16])=[CH:13][CH:14]=2)=[CH:4][C:3]=1[C:18]([F:19])([F:20])[F:21]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 677750201-[4-(4-Chloro-3-trifluoromethylphenoxy)-phenyl]-ethanone

Product 1

HCID 677755811-(4-{[4-Chloro-3-(trifluoromethyl)phenyl]oxy}phenyl)ethanolYield 73.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To the solution of 1-(4-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}phenyl)ethanone (3.12 g, 9.91 mmol) in Ethanol (60 ml), was added NaBH4 (0.450 g, 11.90 mmol). The solution was stirred at room temperature under nitrogen for 1 h. After removing the solvent, the residue was dissolved in DCM, then washed with water twice. The solvent was dried over Na2SO4, concentrated to afford the title compound (2.3 g, 73.2% yield) as light yellow oil. LCMS: rt=3.63 min, [M+H+]=299

Workup

  1. customAfter removing the solvent
  2. dissolutionthe residue was dissolved in DCM
  3. washwashed with water twice
  4. dry with materialThe solvent was dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-dd711d00891748e1848636786ed12bc2
Source dataset
uspto-grants-2015_11
Patent number
US09174968B2

Reaction notes

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