4-Fluorobenzaldehyde → 5724-03-8

HRID 1987236Notes

Reaction equation

HRID 1987236 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH:10]([Mg]Br)=[CH2:11]>O1CCCC1>[F:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]([OH:7])[CH:10]=[CH2:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 680234-FluorobenzaldehydeHCID 178418507HCID 178418507, compound

Product 1

HCID 150949505724-03-8

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 4-fluorobenzaldehyde (8.5 g, 68.2 mmol, Aldrich) in 50 mL of tetrahydrofuran was added dropwise to a solution of vinylmagnesium bromide (9.84 g, 75 mmol, Aldrich) in 150 mL of tetrahydrofuran at 0° C. The mixture was stirred for min and then allowed to warm to room temperature. The reaction was stirred overnight and quenched by the addition of water (100 mL). The resulting precipitate was removed by filtration. The filtrate was concentrated in vacuo and then dissolved in 200 mL of ethyl acetate. This solution was washed with water, brine, dried over sodium sulfate, and concentrated in vacuo to 10.3 g of an amber oil as product. NMR (300 MHz, CDCl3) δ 7.37-7.29 (m, 2H), 7.04 (dd, 2H, J=9 Hz, 9 Hz), 6.08-5.97 (m, 1H), 5.35 (d, 1H, J=17 Hz), 5.21 (d, 2H, J=10 Hz), 1.90 (d, 1H, J=4 Hz).

Workup

  1. stirringThe reaction was stirred overnight
  2. customquenched by the addition of water (100 mL)
  3. customThe resulting precipitate was removed by filtration
  4. concentrationThe filtrate was concentrated in vacuo
  5. dissolutiondissolved in 200 mL of ethyl acetate
  6. washThis solution was washed with water, brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo to 10.3 g of an amber oil as product

Sources & evidence

ORD record
ord-01fbf49db005448ea2257642c678cdf5
Source dataset
uspto-grants-2009_06
Patent number
US07550500B2

Reaction notes

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