2,4-Difluorobenzaldehyde → HCID 65416705, compound

HRID 735326Notes

Reaction equation

HRID 735326 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH:11]([Mg]Cl)=[CH2:12]>O1CCCC1>[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH:4]([OH:5])[CH:11]=[CH2:12]

Participants

4

Reactant 2

HCID 737702,4-DifluorobenzaldehydeHCID 178461836HCID 178461836, compound

Product 1

HCID 65416705HCID 65416705, compoundYield 67.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2,4-Difluorobenzaldehyde (1.42 g, 10 mmol) was dissolved in tetrahydrofuran (20 mL) and cooled to 0° C. Vinyl magnesium chloride (1M in tetrahydrofuran, 12 mL, 12 mmol) was added. The reaction was stirred for 30 minutes then quenched with saturated aqueous ammonium chloride. The mixture was extracted with ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4 and evaporated. The residue was purified by flash column chromatography on silica, eluting with 10% ethyl acetate/isohexane, to give 1-(2,4-difluorophenyl)prop-2-en-1-ol (1.15 g). 1H NMR (500 MHz, CDCl3) δ 7.45-7.39 (1H, m), 6.90-6.86 (1H, m), 6.81-6.77 (1H, m), 6.07-6.00 (1H, m), 5.48 (1H, d, J=5.1 Hz), 5.35 (1H, d, J=17.1 Hz), 5.23-5.20 (1H, m), 2.06 (1H, s).

Workup

  1. customthen quenched with saturated aqueous ammonium chloride
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe residue was purified by flash column chromatography on silica
  7. washeluting with 10% ethyl acetate/isohexane

Sources & evidence

ORD record
ord-8fec22519ed14e72a495b101f1481486
Source dataset
uspto-grants-2009_09
Patent number
US07592456B2

Reaction notes

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