1-(2,6-Dichloro-3-fluorophenyl)ethanone → 1-(2,6-Dichloro-3-fluorophenyl)ethan-1-ol

HRID 2266654Notes

Reaction equation

HRID 2266654 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[C:9]([F:10])=[CH:8][CH:7]=[C:6]([Cl:11])[C:5]=1[C:12](=[O:14])[CH3:13]>CO>[Cl:3][C:4]1[C:9]([F:10])=[CH:8][CH:7]=[C:6]([Cl:11])[C:5]=1[CH:12]([OH:14])[CH3:13]

Participants

4

Reactant 2

HCID 27339821-(2,6-Dichloro-3-fluorophenyl)ethanoneHCID 4311764Sodium borohydride

Product 1

HCID 167700681-(2,6-Dichloro-3-fluorophenyl)ethan-1-olYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium borohydride (90 mg, 2.4 mmol) was added to a solution of 2′,6′-dichloro-3′-fluoro-acetophenone (Aldrich, catalog # 52,294-5) (207 mg, 1 mmol) in 2 mL of anhydrous CH3OH. The reaction mixture was stirred at room temperature for 1 h then was evaporated to give a colorless oil residue. The residue was purified by flash chromatography (eluting with 0→10% EtOAc in hexanes) to give compound A1 as a colorless oil (180 mg; 0.88 mmol; 86.5% yield); MS (APCl) (M−H)− 208; 1H NMR (400 MHz, chloroform-D) δ ppm 1.64 (d, J=6.82 Hz, 3H) 3.02 (d, J=9.85 Hz, 1H) 6.97-7.07 (m, 1H) 7.19-7.33 (m, 1H).

Workup

  1. customthen was evaporated
  2. customto give a colorless oil residue
  3. customThe residue was purified by flash chromatography (eluting with 0→10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-cad78862eac348bb9dfa855e5af44631
Source dataset
uspto-grants-2010_12
Patent number
US07858643B2

Reaction notes

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