3-Chloro-2,6-difluorobenzaldehyde → 1-(3-Chloro-2,6-difluorophenyl)prop-2-en-1-ol

HRID 1481260Notes

Reaction equation

HRID 1481260 reaction equation
[CH:1]([Mg]Br)=[CH2:2].[Cl:5][C:6]1[C:7]([F:15])=[C:8]([C:11]([F:14])=[CH:12][CH:13]=1)[CH:9]=[O:10]>C1COCC1>[Cl:5][C:6]1[C:7]([F:15])=[C:8]([CH:9]([OH:10])[CH:1]=[CH2:2])[C:11]([F:14])=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 7363383-Chloro-2,6-difluorobenzaldehydeHCID 178418507HCID 178418507, compound

Product 1

HCID 867102171-(3-Chloro-2,6-difluorophenyl)prop-2-en-1-olYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 100 mL dry round bottom flask containing vinylmagnesium bromide (1 M in THF) (24 mL, 24.00 mmol) under Ar at 0° C. was added 3-chloro-2,6-difluorobenzaldehyde (3.2 g, 18.13 mmol) in THF (10 mL) dropwise. The reaction was stirred for 1 h and quenched with 1 N HCl to pH 2. The mixture was extracted with Et2O (3×). The combined organic layer was washed with brine, dried over MgSO4, filtered, and concentrated to yield the desired product (3.71 g, 100%) as pale yellow oil. 1H NMR (500 MHz, CDCl3) δ 7.34 (ddd, J=8.9, 8.1, 5.8 Hz, 1H), 6.90 (td, J=9.2, 1.7 Hz, 1H), 6.23 (dddt, J=17.2, 10.4, 5.8, 1.2 Hz, 1H), 5.60 (dd, J=7.6, 6.7 Hz, 1H), 5.40-5.31 (m, 1H), 5.28 (dt, J=10.2, 1.2 Hz, 1H), 2.38 (dt, J=8.3, 1.9 Hz, 1H).

Workup

  1. customTo a 100 mL dry round bottom flask
  2. customquenched with 1 N HCl to pH 2
  3. extractionThe mixture was extracted with Et2O (3×)
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-10cfc6300d704d2788210f2ec692faae
Source dataset
uspto-grants-2016_08
Patent number
US09409908B2

Reaction notes

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